Vacation rentals in Sarasota, FL with free parking

Explore 940 vacation rentals, homes, and villas with free parking in Sarasota, FL for your next getaway or business trip. With on-site parking included in your stay, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Homes with Pools and Best Affordable Homes. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. With options starting as low as $48 per night and homes offering up to 15 bedrooms and 17 bathrooms, it's easy to book a personalized stay designed for your comfort. With 24/7 local support and high-speed Wi-Fi, you can also stay connected and protected throughout your trip. Plus, Marriott Bonvoy members earn points on every stay, making each trip more rewarding than the last. Book your next stay with ease and enjoy the convenience of free parking.

940 Homes with Free Parking in Sarasota

Modern Luxury, Walk to Downtown, Minutes to Beach and Bay

Sarasota, Florida, US
2 Bedrooms 6 Guests
Aug 17 - 24
$308 night

Welcome to Coastal Moderne, a sophisticated four-story townhouse with a private rooftop with gas grill and sunset views, perfectly positioned in the heart of vibrant Downtown Sarasota! This modern 2-bedroom, 2.5-bath home was thoughtfully designed with comfort and convenience in mind. Walking distance to Downtown’s top restaurants, shopping, weekend farmer’s markets, nightlife, live music, and more! Perfect for a luxury retreat or the business traveler looking for an elevated experience. Contemporary decor throughout the open floor plan and a private rooftop with an outdoor kitchen and gorgeous views of the city. Ideal for families, couples, business professionals, extended stays, and vacationers seeking an upscale urban getaway. - Rooftop Dining, Sunset Views, Gas Grill - Near Top Beaches: Siesta Key, Lido Key, Longboat Key - Fully Stocked Gourmet Kitchen - In-Home Private Laundry Room - High-End Furnishings - King and Queen Bedrooms with High-Quality Linens - Ensuite Bathrooms with Plush Towels - High Speed Internet - Smart TVs and Streaming - Pet Friendly - Perfect For Business Travelers - Central Downtown Location - Minutes from St Armands Circle With its unbeatable location you are just a short walk or quick trolley ride to Downtown Sarasota’s best restaurants, shopping, rooftop bars, nightlife, and weekly farmer’s market. The famous St. Armand’s Circle is a quick drive, and the top-rated Siesta Key and Lido Key Beaches are just minutes away. For the adventure seeker you are just minutes from Payne Park, The Legacy Trail, Selby’s Botanical Gardens, and Bayfront Park offer plenty of outdoor activities. Just steps from the townhome is the Bay Runner trolley stop, a free, open-air and scenic ride to Downtown Sarasota, St. Armand’s Circle, Lido Beach, and more. THE INTERIOR SPACE ----------------------- Welcoming entryway with queen sleeper sofa, and garage access. Second Floor - Open Concept Living - Chef’s Kitchen: State-of-the-art appliances, sleek cabinetry, and a large island with seating, perfect for cooking and gatherings. Stocked with all the kitchen essentials you need for your stay. - Bright Living + Dining: Spacious living area with SMART TV and fireplace opens up to the kitchen and large elegant dining space. Third Floor – Tranquil Retreat - Primary Suite: King bed with fresh hotel-style linens, seating area, luxurious ensuite bathroom with plush bath towels, and large walk-in closet. - Guest Bedroom: Queen bedroom with Smart TV and guest bathroom just steps away. Stocked with bathroom essentials and fresh towels. LOCAL ATTRACTIONS ------------------------ - Sarasota Pompano Park Pickleball Courts - Legacy Trail - Siesta Key Beach - Lido Key Beach - Downtown Sarasota - St Armands Circle - Sarasota Jungle Gardens - John Ringling Museum GOLF AND COUNTRY CLUBS ---------------------------- - The Meadows - University Park Country Club - Tatum Ridge - IMG Academy Golf Club - Esplanade Golf - Waterleaf LOCAL GROCERY ------------------- - Detwiler’s Farm Markets: Great for organic fruits and vegetables! - Publix - Trader Joes - Whole Foods - Fresh Market - Walmart Grocery ADDITIONAL AMENITIES ---------------------------- - Fresh Hotel-Style Linens - Plush Towels and Washcloths - Starter of Bath Essentials - soap, shampoo & conditioner - Paper Towels, Dish Soap, Kitchen Sponge - Trash Bags - Local Coffee - Laundry Detergent * Please be prepared to bring any additional supplies that you will need during your stay. Thank you! AREA ATTRACTIONS ----------------------- - 12 miles from IMG Academy - 1 minute from Downtown Sarasota - 2 minutes from Payne Park - 1 mile from Bayfront Park - 1 mile from Marie Selby Botanical Gardens - 1 mile from the Ritz-Carlton and Westin Hotels - 3 miles from Bobby Jones Golf Club - 11 miles to Waterside at Lakewood Ranch AIRPORTS ------------ - 5 Miles from Sarasota-Bradenton International Airport (SRQ) - 63 miles from Tampa International Airport (TPA) BEACHES ------------- - Lido Key Beach (4 miles) - Siesta Key Beach (7 miles) - Turtle Beach (9 miles) - Longboat Key Beach (10 miles) - Anna Maria Island (20 miles) PET FRIENDLY ---------------- This is a pet friendly home! Please include your pet in your booking so we can make the appropriate arrangements for the departure cleaning. A $125 pet fee per dog is required to help remove pet hair and dander from any furnishings and floors for our future guests. Thank you for your understanding, and we look forward to hosting you and your pup! PRIVATE ELEVATOR ---------------------- PLEASE NOTE: Elevators are subject to wear and tear as they have complex mechanical parts and could malfunction if not used properly causing temporary interruptions in service. While we address maintenance and repairs promptly, please be aware that you may have to use the stairs during your stay. If you or a guest has mobility issues please contact us for other rental options - thank you! WELCOME TO SARASOTA! ---------------------------- Considered one of the top places to visit in Florida, Sarasota is home to white sandy beaches, crystal clear waters from the Gulf Coast and a diverse community full of enriching arts and culture. The Sarasota beaches are comprised of six islands, each with their own unique personality, natural beauty, and fun adventures. Longboat Key is the northernmost key with 12 miles of sandy shores and a place sea turtles come to nest. Lido Key has three beaches and home to the famed St. Armand’s Circle. Siesta Key has two main bridges and is regarded as the #1 beach in the world. Caspersen Beach in Venice is dog-friendly and the perfect place for shark tooth hunters. Manasota Key is the nature lovers dream with walking trails from Gulf to bay. And finally, Casey Key has an 18-acre park, picnic areas and concession stand, perfect for a fun day trip. After a day enjoying one of the many beaches, explore another side of Sarasota- the arts, restaurants, and nightlife. Known as Florida’s Cultural Coast, Sarasota County has an array of museums, galleries and performing art venues. For the foodie in all of us, enjoy several award-winning restaurants with views of the Gulf, skyline and more. From fine dining to small seafood joints and numerous food festivals, there is an abundance of choices.

Luxury 4 Story Townhome, Private Rooftop Deck with Outdoor Kitchen, Furniture and Jacuzzi. Short Walk to Beach Shuttle and Vibrant Downtown Sarasota

Sarasota, FL, US
4 Bedrooms 10 Guests
Aug 17 - 24
$562 night

Welcome to Uptown Luxury on Audubon in beautiful Downtown Sarasota! This luxury 4-story 4 bedroom, 3.5 bathroom townhome offers a perfect blend of urban chic and modern elegance. Located in the vibrant Uptown District of Downtown Sarasota this townhome is perfectly positioned within walking distance of Downtown’s top amenities and attractions. With bustling shops, top restaurants, boutiques, annual festivals, weekly famer’s market, and excellent nightlife and live music, you’ll find yourself in the heart of all the action. Perfect for business travelers, remote workers, couples, or friends looking to explore the best of Sarasota. - Rooftop Hot Tub, Grill, Seating, Outdoor Kitchen with Sunset Views - Near Top Beaches: Siesta Key, Lido Key, Longboat Key - Fully Stocked Gourmet Kitchen - Large Kitchen Island with Seating - In-Home Private Laundry Room - High-End Furnishings - King and Queen Bedrooms with High-Quality Linens - Ensuite Bathrooms with Plush Towels - High Speed Internet - Smart TVs and Streaming - Wine Fridge and Wet Bar - Private Balconies - 2 Car Garage - Pet Friendly - Perfect For Business Travelers - Central Downtown Location - Minutes from St Armands Circle - Trolly Access THE INTERIOR SPACE ------------------------- The open-concept design is perfect for socializing and entertaining, with two distinct living areas and a formal dining room. The townhome boasts a number of luxurious amenities, including a wine cooler and wet bar, perfect for entertaining and enjoying your favorite beverages. One of the highlights of this vacation rental is the stunning panoramic views of downtown Sarasota and the picturesque Sarasota Bay. Here you will witness breathtaking sunsets from your own private rooftop deck, which features a relaxing hot tub, an outdoor kitchen and grill. Whether you’re hosting a barbecue party or just enjoying a peaceful evening with loved ones, this rooftop oasis will undoubtedly be a highlight of your stay. The rooftop deck is thoughtfully furnished with sun loungers and ample seating, including an outdoor sectional and a high-top dining table, perfect for al fresco dining or sipping cocktails under the stars. If you’re keen on exploring the surrounding areas, you’re in luck! The townhouse is conveniently situated near a trolley stop, providing easy access to popular destinations like St. Armands Circle and Lido Beach. Additionally, the trolley makes frequent stops at downtown restaurants, bars, and boutiques, ensuring you can easily immerse yourself in the local culture and entertainment. The popular Legacy Trail and vibrant Main Street are just steps away from your private retreat. Inside the rental, you’ll discover a wealth of 5-star amenities to make your stay truly luxurious. Plush linens, premium toiletries, and a fully stocked gourmet kitchen with island seating will ensure you have everything you need for a comfortable and convenient stay. The bedrooms are tastefully appointed, with two kings, two queens, and one double bed, all promising a restful night’s sleep after a day of adventure or relaxation. The primary bedroom boasts a unique touch with a Japanese shower and a private terrace, providing an intimate space to unwind and take in the serene surroundings. With its ideal location, modern elegance, and top-notch amenities, this vacation rental is the perfect choice for your next getaway to Sarasota. Whether you’re seeking a relaxing retreat or an exciting urban adventure, this luxury townhome promises an unforgettable experience for you and your loved ones. Book now and embark on a journey of indulgence and bliss in this captivating Sarasota gem. LOCAL ATTRACTIONS ------------------------ - Sarasota Pompano Park Pickleball Courts - Legacy Trail - Siesta Key Beach - Lido Key Beach - Downtown Sarasota - St Armands Circle - Sarasota Jungle Gardens - John Ringling Museum GOLF AND COUNTRY CLUBS ---------------------------- - Bobby Jones - The Meadows - University Park Country Club - Tatum Ridge - IMG Academy Golf Club - Esplanade Golf - Waterleaf LOCAL GROCERY ------------------- - Detwiler’s Farm Markets: Great for organic fruits and vegetables! - Publix - Trader Joes - Whole Foods - Fresh Market - Walmart Grocery ADDITIONAL AMENITIES ---------------------------- - Fresh Hotel-Style Linens - Plush Towels and Washcloths - Turkish Beach Towels - Starter of Bath Essentials - Soaps, Shampoo, Conditioner - Paper Towels, Dish Soap, Kitchen Sponge - Trash Bags - Local Coffee - Laundry Detergent * Please be prepared to bring any additional supplies that you will need during your stay. Thank you! AREA ATTRACTIONS ----------------------- - 12 miles from IMG Academy - 1 minute from Downtown Sarasota - 2 minutes from Payne Park - 1 mile from Bayfront Park - 1 mile from Marie Selby Botanical Gardens - 1 mile from the Ritz-Carlton and Westin Hotels - 3 miles from Bobby Jones Golf Club - 11 miles to Waterside at Lakewood Ranch AIRPORTS ------------ - 5 Miles from Sarasota-Bradenton International Airport (SRQ) - 63 miles from Tampa International Airport (TPA) BEACHES ------------- - Lido Key Beach (4 miles) - Siesta Key Beach (7 miles) - Turtle Beach (9 miles) - Longboat Key Beach (10 miles) - Anna Maria Island (20 miles) PET FRIENDLY ---------------- This is a pet friendly home! Please include your pet in your booking so we can make the appropriate arrangements for the departure cleaning. A $125 pet fee per dog is required to help remove pet hair and dander from any furnishings and floors for our future guests. Thank you for your understanding, and we look forward to hosting you and your pup! PRIVATE ELEVATOR ---------------------- PLEASE NOTE: Elevators are subject to wear and tear as they have complex mechanical parts and could malfunction if not used properly causing temporary interruptions in service. While we address maintenance and repairs promptly, please be aware that you may have to use the stairs during your stay. If you or a guest has mobility issues please contact us for other rental options - thank you! WELCOME TO SARASOTA! ---------------------------- Considered one of the top places to visit in Florida, Sarasota is home to white sandy beaches, crystal clear waters from the Gulf Coast and a diverse community full of enriching arts and culture. The Sarasota beaches are comprised of six islands, each with their own unique personality, natural beauty, and fun adventures. Longboat Key is the northernmost key with 12 miles of sandy shores and a place sea turtles come to nest. Lido Key has three beaches and home to the famed St. Armand’s Circle. Siesta Key has two main bridges and is regarded as the #1 beach in the world. Caspersen Beach in Venice is dog-friendly and the perfect place for shark tooth hunters. Manasota Key is the nature lovers dream with walking trails from Gulf to bay. And finally, Casey Key has an 18-acre park, picnic areas and concession stand, perfect for a fun day trip. After a day enjoying one of the many beaches, explore another side of Sarasota- the arts, restaurants, and nightlife. Known as Florida’s Cultural Coast, Sarasota County has an array of museums, galleries and performing art venues. For the foodie in all of us, enjoy several award-winning restaurants with views of the Gulf, skyline and more. From fine dining to small seafood joints and numerous food festivals, there is an abundance of choices.

Amazing City Views from the Rooftop, Jacuzzi, Walk to Downtown

Sarasota, Florida, US
2 Bedrooms 6 Guests
Aug 17 - 24
$303 night

Experience the best of Sarasota from Papaya Place, a stylish four-story luxury townhome located in the heart of vibrant Downtown Sarasota. Designed for comfort, convenience, and elevated living, this modern two-bedroom, two-and-a-half-bath retreat is the perfect home base for couples, families, business travelers, extended stays, and vacationers looking for a sophisticated urban escape. Step outside and you’re within walking distance of Downtown Sarasota’s top restaurants, boutique shopping, weekend farmers markets, nightlife, live music, rooftop bars, and more. After a day of exploring, return home to relax in the beautifully designed open-concept living space or head to your private rooftop terrace to fire up the gas grill, enjoy an outdoor meal, soak in the hot tub, and take in stunning sunset and city views. Highlights & Amenities • Private rooftop terrace with gas grill, dining area, hot tub and sunset views • Fully stocked gourmet kitchen with modern appliances • King primary bedroom and queen guest bedroom • Queen pullout couch • High-quality linens and plush towels • Contemporary décor and high-end furnishings • Private in-home laundry room • High-speed Wi-Fi • Smart TVs with streaming capabilities • Pet friendly • 2 Car Garage with Condo Access • Ideal for business travelers and extended stays • Prime Downtown Sarasota location • Minutes from Siesta Key, Lido Key, and Longboat Key beaches • Quick access to St. Armands Circle Location, Location, Location Papaya Place puts you in the center of everything Sarasota has to offer. Walk to Downtown’s best restaurants, shops, nightlife, entertainment, weekly farmers markets, and live music. The nearby Bay Runner trolley stop provides a free, open-air, scenic ride to Downtown Sarasota, St. Armands Circle, Lido Beach, and other popular destinations. The famous St. Armands Circle is just a short drive away, while the beautiful beaches of Siesta Key, Lido Key, and Longboat Key are only minutes from the townhome. Outdoor enthusiasts can enjoy nearby Payne Park, The Legacy Trail, Marie Selby Botanical Gardens, and Bayfront Park, offering opportunities for walking, biking, sightseeing, and enjoying Sarasota’s beautiful natural surroundings. The Interior Space The welcoming entryway offers a comfortable chaise that opens to a queen and convenient garage access. On the second floor, the open-concept living area creates a bright and inviting space where the kitchen, dining area, and living room flow seamlessly together. The chef’s kitchen features sleek cabinetry, modern appliances, a large island with seating, and all the essentials needed to prepare everything from a quick breakfast to a gourmet dinner. The spacious living area includes comfortable furnishings, a Smart TV, and a cozy fireplace, while the elegant dining area provides the perfect setting for meals and gatherings. The third floor offers a peaceful retreat after a day of adventure. The primary suite features a luxurious king-size bed with hotel-quality linens, a comfortable seating area, large walk-in closet, and a beautifully appointed ensuite bathroom stocked with plush towels. The inviting guest bedroom features a queen/twin bunk bed, Smart TV, and easy access to the guest bathroom, which includes fresh towels and essential amenities. The crowning feature of Papaya Place is the private rooftop terrace. Grill dinner, dine outdoors, relax with a cocktail, unwind in the jacuzzi, and watch the sunset over Sarasota from your own private retreat. Whether you’re visiting for the beaches, dining, arts, nightlife, business, or simply a relaxing getaway, Papaya Place offers the perfect combination of luxury, style, and location for an unforgettable Sarasota stay. AREA ATTRACTIONS ----------------------- - 12 miles from IMG Academy - 1 minute from Downtown Sarasota - 2 minutes from Payne Park - 1 mile from Bayfront Park - 1 mile from Marie Selby Botanical Gardens - 1 mile from the Ritz-Carlton and Westin Hotels - 3 miles from Bobby Jones Golf Club - 11 miles to Waterside at Lakewood Ranch AIRPORTS ------------ - 5 Miles from Sarasota-Bradenton International Airport (SRQ) - 63 miles from Tampa International Airport (TPA) BEACHES ------------- - Lido Key Beach (4 miles) - Siesta Key Beach (7 miles) - Turtle Beach (9 miles) - Longboat Key Beach (10 miles) - Anna Maria Island (20 miles) PET FRIENDLY ---------------- This is a pet friendly home! Please include your pet in your booking so we can make the appropriate arrangements for the departure cleaning. A $125 pet fee per dog is required to help remove pet hair and dander from any furnishings and floors for our future guests. Thank you for your understanding, and we look forward to hosting you and your pup! PRIVATE ELEVATOR ---------------------- PLEASE NOTE: Elevators are subject to wear and tear as they have complex mechanical parts and could malfunction if not used properly causing temporary interruptions in service. While we address maintenance and repairs promptly, please be aware that you may have to use the stairs during your stay. If you or a guest has mobility issues please contact us for other rental options - thank you!

Pineapple Paradise #2 • 13 min to Beach • Fire Pit

Sarasota, FL, US
1 Bedrooms 2 Guests
Aug 17 - 19
$104 night

This 1-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Shared Outdoor Patio • Fire Pit • Hammock • Dedicated Workspace • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Bed • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Dog Friendly • Street Parking - 1 car Welcome to Pineapple #2 – Your Sarasota Escape! This charming 1-bedroom, 1-bathroom apartment offers a cozy retreat perfect for up to 2 guests. Whether you’re in town for a beach getaway, a romantic escape, or just a relaxing stay, Pineapple 2 provides the comfort and convenience you need. Step outside and enjoy the inviting shared backyard, where you can unwind around the gas fire pit table, swing gently in the hammock, or simply soak up the Florida sunshine. As this is a shared space, you may also meet fellow travelers enjoying the area. Conveniently located in the heart of Sarasota, you’ll be just minutes from pristine beaches, Historic Downtown dining, boutique shopping, and cultural attractions. Pineapple 2 is the perfect spot to relax, recharge, and experience all that Sarasota has to offer! MAIN SPACES OF THE HOME: – 1 BEDROOM & 1 BATHROOM– BEDROOM 1: * Full-sized Bed * Nightstand and Lamps * Mirror * Ensuite Bathroom – 1 BATHROOM – * Ensuite Bathroom with Walk-in Shower – CHEF’S KITCHEN – * Fully Stocked * High-end Appliances * Large Refrigerator * Ample Cabinetry * Coffee Maker: Drip & Keurig – LIVING ROOM – * Smart TV * Plush Sofa + Seating * Dedicated Workspace * Open Floor Plan The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Check-in is at 4pm Check-out is at 10am - 1 dog is allowed for $125 per stay, no cats please. We kindly ask that your dog be trained and that you pick up after your dog. - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - Parking in the street for 1 car max. Street parking allowed: yes - If you’re interested in a long-term stay, please reach out to inquire about availability. - Guests must be 25 years or older to book this property. - Please note that the backyard is a shared space, so other guests may also be enjoying the area during your stay. GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out.

Pineapple Paradise - 13 min to Beach - Fire Pit

Sarasota, FL, US
3 Bedrooms 8 Guests
Aug 17 - 19
$231 night

This unique combination of three homes offers a total of 3 bedrooms, is in a prime location, and has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Shared Outdoor Patio • Fire Pit • Hammock • Dedicated Workspace • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Beds • High Speed WIFI • Family Friendly-High Chair & Pack ’n Play • Dog Friendly • Street Parking Welcome to Pineapple Paradise #1–3, a unique Sarasota retreat comprising three private homes combined into one stay, perfectly designed for groups seeking space, privacy, and a prime location. This thoughtfully arranged getaway offers a total of 3 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests—ideal for families, friends, or couples traveling together who appreciate having separate spaces under one booking. Located in the heart of downtown Sarasota, you’re just minutes from world-class beaches, vibrant dining, shopping, arts, and nightlife. Whether you’re heading to Lido Beach, exploring St. Armands Circle, or enjoying Sarasota’s cultural scene, Pineapple Paradise places you close to it all while providing a relaxed home base to unwind. Enjoy the flexibility of multiple living spaces, the convenience of a central location, and the charm of a one-of-a-kind setup. This is your perfect Florida escape! MAIN SPACES OF THE HOME: – 3 BEDROOMS & 3 BATHROOMS – Pineapple Paradise #1 BEDROOM 1: * Full-sized Bed * Nightstand and Lamps * Mirror Pineapple Paradise #2 BEDROOM 2: * Full-sized Bed * Nightstand and Lamps * Mirror * Ensuite Bathroom Pineapple Paradise #3 BEDROOM 3: * Full-sized Bed * Nightstand and Lamps * Mirror * Ensuite Bathroom – 3 BATHROOMS – * Full Bathroom with Walk-in Shower * Ensuite Bathroom with Walk-in Shower * Ensuite Bathroom with Walk-in Shower – CHEF’S KITCHEN – * Fully Stocked * High-end Appliances * Large Refrigerator * Ample Cabinetry * Coffee Maker: Drip & Keurig – LIVING ROOM – * Smart TV * Plush Sofa + Seating * Dedicated Workspace * Open Floor Plan * Queen Size Sleeper Sofa (Pineapple Paradise #3) The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Check-in is at 4pm Check-out is at 10am - 1 dog is allowed for $125 per stay, no cats please. We kindly ask that your dog be trained and that you pick up after your dog. - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - Parking in the street for 3 cars. Street parking allowed: yes - If you’re interested in a long-term stay, please reach out to inquire about availability. - Guests must be 25 years or older to book this property. - Please note that the backyard is a shared space, so other guests may also be enjoying the area during your stay. GUEST VERIFICATION: To ensure a smooth and secure stay, we require the primary guest listed on the reservation to complete a simple screening process within 48 hours of booking confirmation. Please note that your reservation is not confirmed until these steps are completed. Once verified, and prior to check-in, guests will be asked to sign a Rental Agreement that includes: - Agreeing to our rental terms and conditions. - Providing a valid government-issued ID and a matching credit card before check-in. - Paying a non-refundable $60 damage waiver. The damage waiver provides coverage for accidental damage during your stay, as long as it is reported prior to your check-out. This is collected either at the time of payment through the booking platform or afterward, depending on which platform you use to book. The damage waiver covers accidental damage that may occur during your stay. To ensure coverage, all damage must be reported promptly while you’re still at the property. We understand there is normal wear and tear at houses but should anything accidentally break or get stained during your stay please just let us know. Thank you!

Pineapple Paradise #1 • 13 min to Beach • Fire Pit

Sarasota, FL, US
1 Bedrooms 2 Guests
Aug 17 - 19
$103 night

This 1-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Shared Outdoor Patio • Fire Pit • Hammock • Dedicated Workspace • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Bed • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Dog Friendly • Street Parking - 1 car Welcome to Pineapple 1 – Your Sarasota Escape! This charming 1-bedroom, 1-bathroom apartment offers a cozy retreat perfect for up to 2 guests. Whether you’re in town for a beach getaway, a romantic escape, or just a relaxing stay, Pineapple 1 provides the comfort and convenience you need. Step outside and enjoy the inviting shared backyard, where you can unwind around the gas fire pit table, swing gently in the hammock, or simply soak up the Florida sunshine. As this is a shared space, you may also meet fellow travelers enjoying the area. Conveniently located in the heart of Sarasota, just a few minutes walk to the Historic Downtown Sarasota, you’ll be just minutes from pristine beaches, downtown dining, boutique shopping, and cultural attractions. Pineapple 1 is the perfect spot to relax, recharge, and experience all that Sarasota has to offer! MAIN SPACES OF THE HOME: – 1 BEDROOM & 1 BATHROOM– BEDROOM 1: * Full-sized Bed * Nightstand and Lamps * Mirror – 1 BATHROOM – * Full Bathroom with Walk-in Shower – CHEF’S KITCHEN – * Fully Stocked * High-end Appliances * Large Refrigerator * Ample Cabinetry * Coffee Maker: Drip & Keurig – LIVING ROOM – * Smart TV * Plush Sofa + Seating * Dedicated Workspace * Open Floor Plan The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Check-in is at 4pm Check-out is at 10am - 1 dog is allowed for $125 per stay, no cats please. We kindly ask that your dog be trained and that you pick up after your dog. - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - Parking in the street for 1 car max. Street parking allowed: yes - If you’re interested in a long-term stay, please reach out to inquire about availability. - Guests must be 25 years or older to book this property. - Please note that the backyard is a shared space, so other guests may also be enjoying the area during your stay. GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out.

Pineapple Paradise - 2 Units - 13 min to Beach

Sarasota, FL, US
2 Bedrooms 4 Guests
Aug 17 - 19
$185 night

Escape to sunny Sarasota with this one-of-a-kind 2-unit retreat, perfect for families, friends, or multi-generational travelers! Rent both 2-bedroom units for extra space, enjoy flexible accommodations, and experience the ultimate vacation filled with relaxation, fun, and memorable moments together. • Shared Outdoor Patio • Fire Pit • Hammock • Dedicated Workspace • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Beds • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Dog Friendly • Street Parking - 2 cars Welcome to Pineapple 1 & 2, a charming combo listing in the heart of Sarasota—ideal for couples, friends, or a small family traveling together while still enjoying a bit of privacy. This thoughtfully designed retreat offers 2 bedrooms and 2 full bathrooms, comfortably accommodating up to 4 guests. Each unit features a cozy coastal vibe and all the essentials for a relaxing, effortless stay. Located just minutes from downtown Sarasota, you’ll be close to beautiful Gulf beaches, top dining spots, shopping, and the area’s vibrant arts and culture scene. Whether you’re soaking up the sun, exploring the city, or unwinding after a beach day, Pineapple 1 & 2 is the perfect home base. Experience the best of Sarasota—comfort, convenience, and coastal charm all in one place! MAIN SPACES OF THE HOME: – 2 BEDROOMS & 2 BATHROOMS – BEDROOM 1 (Pineapple 1): * Full-sized Bed * Nightstand and Lamps * Mirror BEDROOM 2 (Pineapple 2): * Full-sized Bed * Nightstand and Lamps * Mirror * Ensuite Bathroom – 2 BATHROOMS – * Full Bathroom with Walk-in Shower (Pineapple 1) * Ensuite Bathroom with Walk-in Shower (Pineapple 2) – CHEF’S KITCHEN – * Fully Stocked * High-end Appliances * Large Refrigerator * Ample Cabinetry * Coffee Maker: Drip & Keurig – LIVING ROOM – * Smart TV * Plush Sofa + Seating * Dedicated Workspace * Open Floor Plan The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Check-in is at 4pm Check-out is at 10am - 1 dog is allowed for $125 per stay, no cats please. We kindly ask that your dog be trained and that you pick up after your dog. - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - Parking is available for 2 vehicles in the street. - If you’re interested in a long-term stay, please reach out to inquire about availability. - Guests must be 25 years or older to book this property. - Please note that the backyard is a shared space, so other guests may also be enjoying the area during your stay. GUEST VERIFICATION: To ensure a smooth and secure stay, we require the primary guest listed on the reservation to complete a simple screening process within 48 hours of booking confirmation. Please note that your reservation is not confirmed until these steps are completed. Once verified, and prior to check-in, guests will be asked to sign a Rental Agreement that includes: - Agreeing to our rental terms and conditions. - Providing a valid government-issued ID and a matching credit card before check-in. - Paying a non-refundable $60 damage waiver. The damage waiver provides coverage for accidental damage during your stay, as long as it is reported prior to your check-out. This is collected either at the time of payment through the booking platform or afterward, depending on which platform you use to book. The damage waiver covers accidental damage that may occur during your stay. To ensure coverage, all damage must be reported promptly while you’re still at the property. We understand there is normal wear and tear at houses but should anything accidentally break or get stained during your stay please just let us know. Thank you!

High-end Furnishings, Heated Pool, Mins to Downtown and Beaches

Sarasota, Florida, US
4 Bedrooms 8 Guests
Aug 25 - 29
$545 night

Welcome to Ringside on Ringling! Coastal Luxury in the heart of Sarasota just minutes from Downtown and Florida’s top-rated beaches. Experience the perfect blend of luxury, location, and relaxation at Ringside on Ringling, a beautifully renovated coastal-modern vacation home inspired by Sarasota’s rich circus history. Nestled in one of Sarasota’s most desirable and walkable neighborhoods, you’ll be just minutes from downtown dining, shopping, nightlife, and the area’s award-winning Gulf Coast beaches. Highlights and Amenities • Private heated saltwater swimming pool • Backyard oasis with dining area and pool loungers • Corn hole game for family-friendly fun • Large outdoor dining table and BBQ grill • Fully stocked beach essentials, including: beach chairs, cooler, and umbrella • Walkable to Downtown Sarasota restaurants, shops, galleries, and nightlife • Short drive to Siesta Key, Lido Key, and Sarasota’s top beaches • Located in a highly sought-after, tree-lined neighborhood • Free Trolley for convenient transportation • Near top-rated parks and golf courses • Payne Park Playground and Skate Park just 2-minutes away Interior Features • Completely renovated with a coastal-modern design • High-end furnishings and stylish décor throughout • Spacious open floor plan ideal for families and groups • Large living room featuring: Plush sectional sofa, extra-large SMART TV, dining table with seating for eight, and dedicated wine bar for entertaining Gourmet Kitchen • Fully equipped kitchen with all cooking essentials • Spacious countertops with extra seating and ample storage • Modern appliances, Keurig, French Press, Nespresso and classic drip coffee makers • Perfect for everything from quick breakfasts to family dinners Sleeping Accommodations Primary Suite 1 • King-size bed • SMART TV • Large closet • Private ensuite bathroom with walk-in shower and plush towels and premium linens Primary Suite 2 • King-size bed • SMART TV • Large closet • Private ensuite bathroom • Walk-in shower • Plush towels and premium linens Guest Bedroom 3 • King-size bed • SMART TV • Ample closet storage Guest Bedroom 4 • Two twin beds • SMART TV • Ample closet storage Guest Bathroom • Bathtub and shower combination • Vanity with storage • Soft, plush towels Why Guests Love Ringside on Ringling • Walkable downtown location • Luxury coastal-modern style • Two private king suites • Heated pool and outdoor entertainment space • Sand-resistance Turkish beach towels and beach essentials provided • Close to Sarasota’s best beaches, attractions, dining, and nightlife Whether you’re planning a family vacation, couples’ getaway, or a trip with friends, Ringside on Ringling offers everything needed for an unforgettable Sarasota escape. Hop on the Bay Runner Trolley (only a quick 7-minute walk) and enjoy your free ride to Downtown, over the Ringling Bridge to St. Armand’s Circle, Lido Beach and The Ted Sperling Nature Park for kayaking. Payne Park is also under a 10-minute walk. This 29-acre park is home to the Payne Park Skate Park, a large circus themed playground for children, walking trails, on site cafe and amphitheater. The Legacy Trail is also less than ½ mile from the house, a 22.9 mile paved trail for cyclists, walkers and inline skaters. Some of our favorite public golf courses include University Park CC, Rosedale CC, the new Calusa Country Club (Lakewood Ranch), Bobby Jones, IMG Academy, Waterlefe, Misty Creek, Serenoa and Manatee Golf Course. Sarasota’s Rich Ringling History The name Ringside on Ringling celebrates Sarasota’s connection to the legacy of John Ringling, one of the visionaries behind the famous Ringling Bros. and Barnum and Bailey Circus. Today, visitors can experience that history firsthand at The Ringling, a stunning waterfront estate featuring the Ca’ d’Zan mansion, the Circus Museum, and beautiful art galleries. Guests staying here are just minutes from exploring Sarasota’s vibrant downtown, filled with restaurants, boutiques, and nightlife, as well as nearby world-class beaches. The Ringling legacy blends culture, art, and coastal charm, making this location a unique and memorable destination for vacationers. City of Sarasota 26-VR-000100

Dog & Family Friendly, Updated Home, Walking Distance to Downtown, Payne Park, Short Drive to Beaches

Sarasota, Florida, US
4 Bedrooms 9 Guests
Sep 1 - 4
$347 night

Welcome to Urban Nest on Eighth! A Downtown Sarasota Retreat that is dog-friendly, family-friendly and close to all the fun this area has to offer. This newly renovated vacation home is perfect for families, offering comfortable furnishings, colorful art, and a relaxed coastal vibe. Located within walking distance of Downtown Sarasota’s shops, dining, and popular parks, it’s ideal for exploring the best of the area on foot. Enjoy evenings gathered around the fire pit, cookouts on the grill, and easy beach days with provided beach essentials. Prime Location: • Perfectly situated within walking distance of vibrant Downtown Sarasota, filled with top-rated restaurants, cafés, boutiques, galleries, rooftop bars overlooking the Gulf, live music and nightlife. • Just a quick walk to Payne Park, featuring tennis courts, a circus-themed playground, skate park, and scenic walking trails—a favorite spot for families and furry friends. • A short drive to popular attractions including Marie Selby Botanical Gardens, St. Armands Circle, and Lido Key Beach for a day in the sun. Home Highlights: • Dog-friendly and family-friendly, welcoming guests of all ages (and paws!) to relax and enjoy. • Completely renovated inside and out with a fresh mid-century modern design and all-new furnishings. • Open floor plan creates a bright, airy, and inviting atmosphere perfect for family gatherings. • Comfortable, stylish décor with colorful art and cozy touches throughout. • Large, plush sectional in the living room with SMART TV for movie nights or lounging after exploring Sarasota. Gourmet Kitchen and Dining: • Fully equipped modern kitchen with sleek stainless steel appliances, cookware, utensils, and plenty of kitchen essentials. • Spacious countertops and an open layout with island and seating - ideal for cooking and family gatherings. • Indoor dining area perfect for family breakfasts, casual lunches, or evening dinners. Bedrooms and Bathrooms: • 4 total bedrooms designed for comfort and flexibility: -Primary bedroom: King bed with luxury linens. -Two guest bedrooms: Each with queen beds and stylish décor (one includes a SMART TV). -Kids’ bedroom: Bunk bed with twin over full plus twin trundle for extra sleeping space. • 2 updated bathrooms featuring glass walk-in showers, modern vanities, and plush bath towels provided. Outdoor Living: • Large private fenced in backyard—safe for kids and dogs to play freely. • Brick patio with outdoor dining table and chairs for al fresco meals. • Fire pit area with Adirondack chairs for cozy evenings under the stars. • Gas grill for cookouts and outdoor shower for rinsing off after a day at the beach or park. Extra Amenities: • In-home washer and dryer for guest convenience. • Beach essentials including chairs and towels. • Pack ’n Play for families traveling with little ones. • High-speed Wi-Fi, central A/C, and ample parking. This dog-friendly, family-friendly Sarasota retreat blends modern comfort, convenient location, and relaxed coastal charm, making it the perfect home base for your next Florida getaway. Pet Fee: This is a pet friendly home! Please include your pet in your booking so we can make the appropriate arrangements for the departure cleaning. A $125 pet fee per dog is required to help remove pet hair and dander from any furnishings and floors for our future guests. Thank you for your understanding, and we look forward to hosting you and your pup!

The Castaway Cottage

Sarasota, FL, US
3 Bedrooms 8 Guests
Aug 22 - 29
$206 night

Experience the perfect Sarasota getaway! This beautifully updated 3-bedroom, 2-bath vacation home combines comfort, convenience, and a prime location just steps from Ed Smith Stadium, home of the Baltimore Orioles Spring Training. Whether you’re planning a family vacation, beach escape, golf trip, or baseball getaway, you’ll love being just minutes from Sarasota’s best attractions. Spend your days lounging by your private screened pool (pool heat available as an add on amenity at $35 plus tax per day and should be arranged at least 3 days prior to check in to allow for scheduling), exploring the vibrant shops and restaurants of Downtown Sarasota, or soaking up the sun on the white sands of Lido Key Beach, located less than 5 miles away. World-famous Siesta Key Beach, St. Armands Circle, and Sarasota’s arts and cultural attractions are all within an easy drive. Inside, the bright, open-concept living space is designed for relaxing after a day of adventure. The comfortable living room features soaring ceilings, plenty of natural light, and a large smart TV for movie nights. The fully equipped kitchen opens to the living area, making it easy to prepare meals while staying connected with family and friends. A spacious dining area provides plenty of seating for everyone. Things To Note- Pet Policy- One well-behaved dog considered with PRIOR approval and $200 pet fee + tax, No cats. Pool Heater- Is available as an add on amenity at $35 plus tax per day and should be arranged at least 3 days prior to check in to allow for scheduling. Stays of greater than 30 nights may require a mid-stay clean and would be arranged through management. VR-24-00135 What Guests Love- Private screened swimming pool Walk to Ed Smith Stadium Less than 5 miles to Lido Key Beach Minutes to Downtown Sarasota, St. Armands Circle & Siesta Key Fully equipped kitchen Smart TVs & high-speed Wi-Fi Driveway parking Bright, open floor plan with vaulted ceilings Quiet residential neighborhood Sleeping Arrangements Primary Bedroom: King Bed with ensuite bath Guest Bedroom: Queen Bed Guest Bedroom: Two Twin Beds (or customize to your actual setup) The Perfect Sarasota Location You’ll be in the heart of everything Sarasota has to offer- Ed Smith Stadium: Walkable- 3–5-minute walk Downtown Sarasota: Approximately 2 miles Lido Key Beach: Less than 5 miles St. Armands Circle: Less than 5 miles Siesta Key Beach: Approximately 7 miles Restaurants, shopping, golf courses, parks, and marinas all nearby. Whether you’re attending Spring Training, enjoying a beach vacation, or exploring Sarasota’s award-winning dining and arts scene, this home offers the ideal home base for your Florida escape. Book your Sarasota vacation today and enjoy the perfect combination of location, comfort, and your own private pool! License: VR-24-00135

Backyard Oasis, Minutes to Beach, Fully Updated

Sarasota, Florida, US
3 Bedrooms 6 Guests
Aug 17 - 24
$261 night

Welcome to your Sarasota coastal retreat—an adorable and charming fully renovated vacation home ideally located just minutes from Downtown Sarasota and the stunning Gulf beaches of Siesta Key and Lido Key. Nestled in a desirable and serene neighborhood shaded by mature trees and lush Florida plant life, this home offers the perfect blend of relaxation, comfort, and convenience. Amenities Include: • Prime location near Downtown Sarasota, Siesta Key and Lido Key • Quiet, tree-lined neighborhood with lush Florida landscaping • Sectional sofa with full-size pullout • Large SMART TVs • Fully equipped kitchen with stainless steel appliances • Backyard with fire pit • Putt-putt golf area • Gas grill • Sun loungers • Screened-in lanai • Foosball table that converts to ping pong • Beach Essentials • Full-size washer and dryer • Primary suite with ensuite bathroom and walk-in closet • Two additional guest bedrooms • Two bathrooms with large walk-in showers • Plush towels, linens and toiletries provided Designed in soothing coastal hues of blues and cream, the interior immediately invites you to unwind. The open floor plan creates a bright and airy atmosphere, perfect for gathering with family and friends. The living area features a plush sectional sofa that easily converts into a full-size pullout bed for additional guests. A large SMART TV anchors the space, making it ideal for movie nights after a day at the beach. Just beyond, the dining area comfortably seats six, creating a welcoming space for shared meals and conversation. The fully equipped modern kitchen boasts stainless steel appliances, generous counter space, and ample storage—everything you need to prepare anything from beach snacks to full dinners. Whether you’re brewing your morning coffee before heading to the shore or hosting a casual evening meal, the kitchen is both stylish and functional. Step outside and discover your private backyard oasis. Designed for fun and relaxation, the yard features a cozy fire pit for evening gatherings, a fun putt-putt golf area for friendly competition, sun loungers for soaking up the Florida sunshine, and a gas grill for outdoor cookouts. The large screened-in lanai extends your living space and includes a foosball table that easily converts to ping pong for hours of entertainment. A full-size washer and dryer are also conveniently located here, making longer stays effortless. The home offers three restful bedrooms designed with comfort in mind. The primary suite features a queen bed, SMART TV, walk-in closet, and a private ensuite bathroom. One guest bedroom includes a comfortable full-size bed, while the third bedroom is perfect for kids or friends with two twin beds and its own SMART TV. Both bathrooms are beautifully updated with large walk-in showers, plush towels, and complimentary toiletries to enhance your stay. Whether you’re exploring vibrant Downtown Sarasota, relaxing on the world-famous beaches of Siesta Key, or enjoying sunsets on Lido Key, this charming coastal home is the perfect place to call your home away from home. City of Sarasota VR25-00111

Sunshine Bungalow

Sarasota, FL, US
2 Bedrooms 4 Guests
Sep 1 - 8
$133 night

SLEEPING ARRANGEMENTS 2 BR / 2BA / Sleeps 4 Master Bedroom – One queen bed and en-suite bathroom with walk-in shower. Guest Bedroom – One Queen bed with access to the second bathroom ______________________________________________________________________________ AMENITIES NOTE: One well-behaved small dog is welcome WITH PRE-APPROVAL and a pet fee of $200 plus tax. Check with the property manager before booking. NO CATS Professionally cleaned and sanitized per CDC guidelines between each guest stay. PLEASE NOTE- For extended stays of 60 days or more we require a mid-stay clean be done by our cleaners. A member of our team will reach out upon your booking to coordinate the fee and scheduling. Close to Downtown Sarasota, beaches, shopping, nightlife. Close to park/playground and basketball courts. Outdoor patio with seating and ambient lighting. Outdoor fire pit with seating in the private fenced backyard. Separate dining room with table and seating for six. Propane grill for outdoor cooking. 2 Beach Chairs, 1 small cooler, 1 Beach Umbrella Outdoor patio with large dining table and seating for six. Living room with comfy couch and chairs and TV. Fully stocked modern kitchen with everything you need to make meals at home. 1 set of towels (1 bath, 1 hand, and 1 washcloth) are provided per person for the max number of people the home sleeps Stackable washer/dryer combination in the kitchen. High-Speed WIFI included. No Smoking in the home! _____________________________________________________________________________ FULL DESCRIPTION This charming historic 1923 Craftsman Bungalow home near downtown Sarasota, has been newly renovated and decorated. Upon entering the home, you are greeted with a living room with a comfortable seating arrangement. There is a formal dining room with seating for up to six people and an eat-in kitchen towards the rear of the house that is fully stocked with everything you need to make delicious meals at home. The rear door in the kitchen leads to an outdoor dining table with ambient lighting at night for meals al fresco. After dinner, relax with your favorite drink around the firepit in this private backyard. There are two bedrooms with queen size beds and access to the two bathrooms, one with a tub and the other with a walk-in shower in the master bedroom. Both bedrooms are appointed with luxurious sheets and bedding for a restful night’s sleep. With a lovely neighborhood park in walking distance, many guests consider bringing their furry companion along. Dogs are considered with a non-refundable pet fee of $200 plus tax. Please reach out for approval. This comfortable private home is located just minutes from downtown Sarasota where you will find many options for dining, shopping, and nightlife. Take your dog for a stroll to Whitaker Gateway Park within walking distance from the home and includes a nice playground with restrooms, a picnic area. and beautiful views of the bay. No trip to Sarasota would be complete without going to one of the world-class white sand beaches nearby. Siesta Key Beach is 8 miles (20-25 minutes) and Lido Beach is 5 miles (15-20 minutes) from the home. Check out St Armand’s Circle near Lido Beach for additional shopping and great restaurant choices. Flying into Sarasota/Bradenton airport is easy and convenient with direct flights from many cities and is only a 10 minutes drive from the home. This home is listed on the National Historic Registry. City of Sarasota Vacation Rental Registration number: VR24-00205 PLEASE NOTE- For extended stays of 60 days or more we require a mid-stay clean be done by our cleaners. A member of our team will reach out upon your booking to coordinate the fee and scheduling. License: VR24-00205

Vitamin Sea

Sarasota, FL, US
4 Bedrooms 8 Guests
Aug 20 - 27
$182 night

What Guests Love- Private Pool – Optional heat (Nov–Apr) for $35/day + tax; must be scheduled before arrival Screened Lanai – Outdoor seating, ambient lighting, and poolside lounging Propane Grill – Perfect for outdoor cooking Beach Gear – 2 chairs, umbrella, cooler Garage & Parking – One-car garage with automatic opener + driveway parking Fully Stocked Kitchen – Modern appliances, granite countertops, bar seating, plus separate dining area for 6 Spacious Living Room – 2 large sofas, flat-screen TV, and lanai access 1 set of towels (1 bath, 1 hand, and 1 washcloth) are provided per person for the max number of people the home sleeps Laundry Room – Full-size washer/dryer Guest House – Private kitchenette, bathroom, and living area Tech & Comfort – Wi-Fi, Streaming TV, central A/C Pet Friendly – One small, well-behaved dog considered ($200 pet fee + tax, approval required). No cats. No Smoking inside the home Location Highlights 8 minutes → Gillespie Park (dog park, pickleball, tennis, trails, fitness equipment) 6 minutes → Payne Park (dog park, skate park, disc golf, playgrounds, cafe) 5 miles → Lido Beach 7 miles → Siesta Key Beach 20 minutes → Sarasota/Bradenton Airport Close to downtown Sarasota for dining, shopping, and nightlife Welcome to your private Sarasota retreat, featuring a sparkling pool (heat optional), screened lanai, and a detached guest house for ultimate comfort and privacy. The main house offers an open-concept floor plan with a modern kitchen, dining space, and two spacious living rooms with that opens to the lanai. Three bedrooms include a master suite with en-suite bath and two guest rooms with convenient access to a shared bathroom. The guest house by the pool is a perfect setup for extended family, friends, teens, or a nanny. It features a king bed, TV, sofa, kitchenette, washer/dryer, full bath, and a cozy private patio. Whether you’re unwinding by the pool, grilling outdoors, or heading out to enjoy Sarasota’s white-sand beaches, lively downtown, or family-friendly parks, this home is the perfect place to make lasting memories! 4 BR / 3 BA / Sleeps 8 Sarasota FL 34237 Vacation Rental License # 25-VR-000004 Minimum stay duration of 7 days/nights Sleeping Arrangements Master Bedroom – Queen bed with en-suite bathroom Guest Bedroom 1 – Queen bed with en-suite bathroom Guest Bedroom 2 – King bed, shares hallway bath with tub/shower combo Guest Bedroom 3 (Detached Guest House, 320 sq ft) – King bed, King sofa, TV, beverage fridge, table with 2 chairs, washer/dryer, full bathroom, and small private patio/courtyard by the pool Note: Main house also offers a Full-size Sofa Bed Professionally cleaned and sanitized per CDC guidelines between each stay. Extended stays (60+ days) require a mid-stay professional clean (fee applies). License: 425-VR-000004

Walk to Park & Pool: Sarasota Family Home w/ Yard

Sarasota, FL, US
3 Bedrooms 5 Guests
Aug 17 - 24
$175 night

Remote Work Ready | 6 Mi to Siesta Key Village | Fenced Yard | Washer & Dryer Coastal relaxation meets active living at this sunny Sarasota vacation rental. Enjoy an early morning stroll to Arlington Park, then grab your towels for an afternoon on the powdery white sands of Siesta Beach. After a day of Gulf Coast fun, catch up on work in the office while the kids play in the yard. Ready for more adventure? Spend the day at Sarasota Jungle Gardens or the Ringling Museum! Book your stay today. -- THE PROPERTY -- VR24-00310 OUTDOOR LIVING - Spacious yard (fenced in) - Patio, grill - Walk to neighborhood park & pool INDOOR LIVING - Dedicated office - Smart TVs - Washer & dryer - Central A/C & heating, ceiling fans KITCHEN - Stove, oven, dishwasher, microwave - Drip & French press coffee makers (bring your own coffee) - Cooking basics & spices - Dining table, dishes & flatware ACCESSIBILITY - Single-story home, step-free access PARKING - Carport (1 vehicle) - Driveway (3 vehicles) -- THE LOCATION -- - Quiet dead-end street in a residential Sarasota neighborhood - Walking distance to Arlington Park: community pool (w/ fee), playground, tennis & racquetball courts, dog park, paved trail (Sarasota to Venice) - 2-3 miles to Downtown Sarasota: cafes, dining, shops, Marie Selby Botanical Gardens, Bayfront Park - 6-7 miles to Siesta Key Village: Siesta Beach, Siesta Key Oyster Bar, restaurants & shops - 6 miles to Sarasota Jungle Gardens - 7 miles to Ca' d'Zan & The John and Mable Ringling Museum of Art -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $150 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in SECURITY CAMERA INFORMATION - 1 exterior device - Location: doorbell - Coverage: entryway Licence number: VR24-00310

Walk to Restaurants: Sarasota Home w/ Lanai!

South Sarasota, FL, US
4 Bedrooms 8 Guests
Aug 31 - Sep 5
$211 night

3 Mi to Botanical Gardens | Fenced Backyard Escape to 'The Melrose Sarasota,' a stylish 4-bedroom, 3-bath vacation rental home designed for relaxation and productivity. Sip coffee on the screened patio surrounded by lush tropical greenery, then head out to explore nearby gems like Sarasota Jungle Gardens, championship golf courses, and sugar-sand beaches. Inside, you’ll find a beautifully updated interior with workspaces, making it easy to blend business with leisure in true Sarasota style. -- THE PROPERTY -- DWE6805155 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 queen bed - Bedroom 4: 1 queen bed INDOOR LIVING - Smart TVs w/ cable - Desks, dining room - Board games & books OUTDOOR LIVING - Fenced backyard - Large screened lanai w/ outdoor couches KITCHEN - Stove/oven, refrigerator, dishwasher - Crockpot, microwave, toaster, toaster oven - Coffee maker, hot water pot - Dishware & flatware - Spices, cooking basics GENERAL - Free WiFi (742 Mbps) - Washer & dryer (detergent provided) - Keyless entry - Complimentary toiletries, linens & towels - Central heating & air conditioning - Hair dryer, iron & ironing board - Trash bags & paper towels FAQ - 2 exterior security cameras (facing out) - Quiet hours (after 11:00 PM) ACCESSIBILITY - Single-story home, 1 step to enter PARKING - Driveway (3 vehicles) - RV parking available on-site -- THE LOCATION -- - Less than 1 mile to local restaurants, cafes & bakeries - 4 miles to Bayfront Park - 5 miles to The Ringling Beach House - 6-7 miles to Siesta Key Beach, Lido Key Beach & South Lido County Park - 11 miles to Oscar Scherer State Park - 8 miles to Sarasota Bradenton Int'l Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Please observe quiet hours after 11:00 PM - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story home requires 1 step to enter - Your safety matters. This property features 2 exterior security cameras. These cameras are outward-facing and do not look into any interior spaces. Camera 1 is located above the front door facing the driveway and camera 2 is located above the lanai door facing the backyard. These cameras record video and audio, and will be turned on for your arrival, but then turned off for the remainder of your stay

Siesta Gardens | Outdoor Oasis, Game Room, Central

Sarasota, FL, US
3 Bedrooms 6 Guests
Aug 17 - 20
$280 night

Welcome to Siesta Gardens, a private tropical oasis surrounded by palms, fruit trees, and lush greenery. This 3BR/2BA home features an oversized lanai, outdoor shower, central A/C, and a climate-controlled game room with a Brunswick pool table, 65" TV, JBL Bar 1300, wine cooler, and office space. Enjoy clean, purified water throughout the home with the HALO whole-home filtration system. Minutes to downtown Sarasota, Siesta Key Beach, parks, shops, and dining, offering privacy and convenience. Welcome to Siesta Gardens, your private tropical hideaway in one of Sarasota’s most desirable and walkable neighborhoods. Surrounded by a lush jungle of palms, fruit trees, vibrant plants, and succulents, this three-bedroom, two-bath retreat offers the serenity of an outdoor oasis with the convenience of being close to everything Sarasota has to offer. From the moment you step onto the property, you’ll feel an immediate sense of calm and privacy—despite being in a quiet residential community just minutes from top attractions. The home features an oversized screened-in lanai that functions as its own outdoor living room. Enjoy comfortable lounge seating, a dining table for four, and dreamy sunset views that paint the sky each evening. The backyard’s tropical landscaping creates a peaceful setting perfect for morning coffee, afternoon relaxation, or unwinding under the stars after a day at the beach. You’ll also find an outdoor shower tucked into the greenery, adding to the resort-like experience. Inside, the home is cooled by central A/C and offers an airy, modern layout designed for comfort. The living room is equipped with a JBL Bar 1300 sound system, transforming movies or music into an immersive experience. The kitchen includes upgraded appliances, a wine cooler, and everything you need to cook at home. The third bedroom doubles as a dedicated office, complete with a desk and monitor—ideal for guests working remotely during their stay. A standout feature of Siesta Gardens is its premium HALO whole-home water filtration and conditioning system. Sarasota tap water often carries a strong chlorine smell and taste—something many visitors notice immediately. With HALO, every faucet and shower in the home delivers clean, purified, odor-free water. It’s a luxury most homes in the area don’t offer, providing guests with softer showers, better-tasting water, and an overall elevated experience. The garage has been thoughtfully converted into a climate-controlled game room, featuring a brand-new Brunswick pool table, a 65-inch TV, and a collection of board games to keep everyone entertained. Whether it’s movie night, game night, or friendly competition around the pool table, this space is always a guest favorite. You’ll love the home’s excellent location. Downtown Sarasota is roughly 7 minutes away, offering dining, shopping, and cultural experiences. Siesta Key Beach, ranked among the best beaches in the world, is approximately 12 minutes away, making beach days effortless. St. Armands Circle, Lido Beach, Arlington Park’s community pool, tennis courts, and walking paths, as well as Payne Park, the Legacy Trail, and local coffee shops, are all just a short drive or bike ride from the property. Quiet, private, and perfectly situated, Siesta Gardens delivers the best of Sarasota living—tropical ambiance, modern comfort, incredible outdoor spaces, and unbeatable proximity to beaches, parks, and downtown. It’s the ideal home base for your Florida getaway. You will have access to everything and nothing is shared. Arlington Park is a shared park. We are here if you need anything and are local. City of Sarasota Vacation Rental Certificate - 25-VR-000039

3 Blocks to the Coast! Cozy Sarasota Retreat

Sarasota, FL, US
2 Bedrooms 4 Guests
Aug 17 - 22
$102 night

Escape to this top-floor Sarasota unit for a trip filled with enough sun, sand, and surf to last a lifetime! Offering 2 beds and 1 bath, this vacation rental is perfect for friends and couples looking for a fully equipped, centrally located stay. Slow things down with a scenic stroll along Siesta Key and kayak through lush mangroves, or, for the more adventurous traveler, explore the area with a jet ski or parasailing tour! Back at your vacation rental, enjoy a good night's rest in modern digs. -- THE PROPERTY -- VR2400169 | Central Location | Pet Friendly w/ Fee Bedroom 1: King Bed | Bedroom 2: Queen Bed SHARED PATIO: Outdoor dining, gas grill, lawn games, umbrella KITCHEN: Fully equipped, stainless steel appliances, spices, dishware & flatware, Crock-Pot, toaster, complimentary tea, drip coffee maker w/ coffee INDOOR DETAILS: Flat-screen TV w/ Google Chrome, dining table, modern furnishings, ceiling fans GENERAL: Free WiFi, washer/dryer, towels/linens, hair dryer, iron, trash bag/paper towels, air conditioning FAQ: Stairs required for access, pet fee (paid pre-trip) PARKING: Driveway (2 vehicles), street parking ADDT'L ACCOMMODATIONS: An additional 2-bedroom property for 4 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- BEACHES: Indian Beach (0.3 miles), Lido Key Beach (5.4 miles), Lido Public Beach (6.3 miles), Sarasota Beach (8.9 miles), Siesta Key Beach (9.6 miles), Longboat Key (13.2 miles) MAIN ATTRACTIONS: Sarasota Jungle Gardens (0.2 miles), Smugglers Cove Adventure Golf (0.5 miles), Sarasota Classic Car Museum (1.3 miles), The John & Mable Ringling Museum of Art (1.7 miles), Ca’d’Zan (1.8 miles), Bayfront Park (2.7 miles), Marie Selby Botanical Gardens (3.1 miles), Mote Marine Laboratory & Aquarium (5.9 miles), The Bishop Museum of Science & Nature (9.8 miles), Big Cat Habitat Gulf Coast Sanctuary (10.9 miles) SIGHTSEEING TOURS: Sarasota by Segway (2.2 miles), Discover Sarasota Tours (2.9 miles), Sarasota Biplane Adventures (4.4 miles), Sarasota Bike Tours (5.5 miles), Sarasota Bay Explorers (6.0 miles), South Lido Mangrove Tours (6.1 miles), Siesta Key Watersports (9.1 miles), Fun Boat Tours (9.7 miles) AIRPORT: Sarasota Bradenton International Airport (1.8 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - Pet friendly w/ $100 fee (+ fees & taxes, dogs and cats only, 2 pets max) - No smoking - Pet friendly w/ $150 fee (+ fees & taxes) - No events, parties or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs and may be difficult for guests with limited mobility Licence number: VR24-00169

Coastal Sarasota Condo: Minutes to Beach!

Sarasota, FL, US
2 Bedrooms 4 Guests
Aug 20 - 23
$98 night

Spend your next beach retreat at this sunny Sarasota vacation rental! The condo provides a comfy and modern home base with 2 bedrooms, 1 bathroom, and a fully equipped kitchen for travelers visiting the Florida coast. Relaxing days come naturally thanks to the home's prime location with easy access to walking and bike trails, beaches, and parks. Don’t feel like going out? Whip up a meal on the BBQ with your friends while sipping on your favorite drink and enjoying the sun on the patio! -- THE PROPERTY -- VR2400297 | Pet Friendly w/ Fee | Free WiFi Endless days filled with sun, sand, and surf await you at this chic Sarasota condo with an ideal, central location. Bedroom 1: King Bed | Bedroom 2: 2 Twin Beds SHARED PATIO: Outdoor dining, gas grill INDOOR LIVING: Modern furnishings, Smart TV, dining table, ceiling fans KITCHEN: Fully equipped w/ cooking basics, dishware/flatware, stainless steel appliances, drip coffee maker, toaster, spices GENERAL: Washer/dryer, linens/towels, complimentary toiletries, central air conditioning FAQ: Step-free access, pet fee (paid pre-trip), 1 exterior security camera (facing driveway, off during guest stay) PARKING: Driveway (1 vehicle) ADDT’L ACCOMMODATIONS: An additional 2-bedroom property for 4 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- SAND & SUN: Indian Beach (0.3 miles), Lido Key Beach (5.4 miles), Lido Public Beach (6.3 miles), Sarasota Beach (8.9 miles), Siesta Key Beach (9.6 miles), Longboat Key (13.2 miles) ATTRACTIONS: Sarasota Jungle Gardens (0.2 miles), Smugglers Cove Adventure Golf (0.5 miles), Sarasota Classic Car Museum (1.3 miles), The John & Mable Ringling Museum of Art (1.7 miles), Ca’d’Zan (1.8 miles), Bayfront Park (2.7 miles), Marie Selby Botanical Gardens (3.1 miles), Mote Marine Laboratory & Aquarium (5.9 miles), The Bishop Museum of Science & Nature (9.8 miles), Big Cat Habitat Gulf Coast Sanctuary (10.9 miles) SIGHTSEEING: Sarasota by Segway (2.2 miles), Discover Sarasota Tours (2.9 miles), Sarasota Biplane Adventures (4.4 miles), Sarasota Bike Tours (5.5 miles), Sarasota Bay Explorers (6.0 miles), South Lido Mangrove Tours (6.1 miles), Siesta Key Watersports (9.1 miles), Fun Boat Tours (9.7 miles) AIRPORT: Sarasota Bradenton International Airport (1.8 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - Pet friendly w/ $100 fee (+ fees & taxes, dogs and cats only, 2 pets max) - No smoking - Pet friendly w/ $150 fee (+ fees & taxes) - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Your safety matters. This property features 1 exterior security camera that faces towards the driveway. The camera is outward facing and does not look into interior spaces. The camera does not actively record video or sound while guests are in residence Licence number: VR24-00297

Nicely Updated, Large Home Just Minutes to Siesta Key and Downtown Sarasota, 2 Game Rooms

Sarasota, FL, US
4 Bedrooms 10 Guests
Aug 17 - 24
$446 night

Welcome to our stunning pool home in Sarasota, Florida! This large and spacious 4-bedroom, 2-bath, dog-friendly retreat is perfectly located just 10 minutes away from the world-renowned Siesta Key beaches and the vibrant downtown Sarasota. With its beautiful updates and modern furnishings, this home offers a delightful blend of comfort and style for your vacation. Highlights and Amenities • Spacious open floor plan perfect for Family & Friend Gatherings • Heated swimming pool with pool-side loungers • Pet-friendly with private fenced-in backyard oasis • Outdoor seating areas, and BBQ grill • Fully stocked beach essentials, including beach chairs, cooler, and umbrella • Lightweight Sand Resistant Turkish Beach Towels Provided • High-Quality Linens and Plush Bath Towels • High Speed Internet and Wi-Fi, Smart TVs for Streaming • Close to Downtown Sarasota restaurants, shops, galleries, and nightlife • Short drive to Siesta Key, Lido Key, and Sarasota’s top rated beaches • Pool Table and Ping Pong Tables • Free Trolley for convenient transportation • Near top-rated parks and golf courses As you step inside, you’ll immediately notice the attention to detail and the welcoming ambiance. The house is tastefully decorated throughout, exuding a modern flair that creates an inviting atmosphere for all guests. With its ample space and thoughtful layout, this vacation home comfortably accommodates up to 10 guests, making it an ideal choice for families or groups of friends. The bedrooms in this home are designed with your comfort in mind. There are two bedrooms with king beds, one bedroom with a queen bed, and a fourth bedroom featuring a bunk bed with a trundle. Additionally, there is a queen pullout sofa available for extra sleeping arrangements. Each bedroom is tastefully furnished, providing a cozy and relaxing retreat after a day of exploring the Sarasota area. One of the highlights of this vacation home is the theatre game room, complete with a generously sized 75" SMART TV, gaming console and pullout couch. Whether you’re in the mood for a movie night or some friendly competition, this room offers the perfect space to unwind and have fun. In the oversized two-car garage, you’ll find a pool table and ping pong table, adding to the entertainment options available for you and your guests. The open living area seamlessly combines a spacious living room, a cozy fireplace with comfortable chairs, a formal dining room, and a gourmet kitchen. The kitchen is a chef’s dream, featuring granite countertops, wood cabinetry, and top-of-the-line stainless steel appliances. With a kitchen counter boasting four barstools and an additional eat-in area with bench seating for five, there’s plenty of room for everyone to gather and enjoy meals together. The backyard of this vacation home is a true oasis. Step outside to discover a crystal clear pool, sun loungers, and an outdoor table and chairs, perfect for al fresco dining or simply soaking up the Florida sunshine. A gas grill is provided for those who enjoy cooking outdoors, and an outdoor fireplace adds a touch of warmth and ambiance to your evenings. Surrounding the pool area is a lovely garden, creating a serene and peaceful atmosphere. Whether you’re looking to relax by the private pool, explore the famous beaches, or immerse yourself in the vibrant culture of downtown Sarasota, this vacation home offers the perfect base for your Florida getaway. With its convenient location, modern amenities, and spacious design, you’re sure to create unforgettable memories during your stay in this beautiful Sarasota retreat. Other Things to Note: ---------------------------------------- Pet Fee: This is a pet friendly home. Please include your pet in your booking so we can make the appropriate arrangements for the departure cleaning. A $125 pet fee, per pet is required to help remove pet hair and dander from any furnishings and floors for our future guests. Thank you for your understanding, and we look forward to hosting you and your pup! Pool Heater: We recommend only heating the pool in the months of October through May, as the pool during summer months should not need heating. If you’d like the pool heated during your stay, please let us know at least 24–48 hours before your arrival so we can have it ready for you. A $12 daily heating fee applies to help cover energy costs. Please note, if you request heating after check-in, a $50 service fee will be added for our team to come out and activate the heater. Dogs are not allowed in the pool at any time as the filtration system is not designed for filtering pet hair. Thank you for your understanding—we want to ensure you enjoy a comfortable and relaxing swim! ---------------------------------------- City of Sarasota VR24-00154

’Vintage Mermaid Cottage’ 4 Mi to Siesta Key Beach

Sarasota, FL, US
2 Bedrooms 6 Guests
Aug 17 - 24
$126 night

Great for Snowbirds | Beach Gear Provided | 3 Mi to Downtown Sarasota Sun-soaked days and salty breezes are calling! This charming Sarasota vacation rental is the perfect launchpad for your coastal getaway. Visit the world-famous Siesta Key Beach, greet the sea creatures at Mote Marine Laboratory, or enjoy a romantic stroll through Marie Selby Botanical Gardens. There's something for everyone! As the sun sets, gather your crew on the patio and share your favorite stories. Paradise awaits! -- THE PROPERTY -- VR24-00145 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed  - Bedroom 2: 1 king bed - Living Room: 1 full sleeper sofa OUTDOOR LIVING  - Patio w/ seating & table - Yard w/ lounge seating INDOOR LIVING  - 4 Smart TVs - 2 living areas - 2 dining tables, breakfast bar - Books - En-suite bathroom, walk-in closet KITCHEN  - Stove/oven, refrigerator - Microwave, toaster - Keurig coffee maker (starter pods provided) - Cooking basics, dishware/flatware GENERAL   - Free WiFi  - Central air conditioning/heat - Linens/towels, hair dryer - Washer/dryer, iron/board FAQ - Quiet hours (after 11:00 PM) - Exterior security camera (facing front entrance) - Pet fee (paid pre-trip) - Long-term tenant on-site (behind cottage) ACCESSIBILITY - Single-story home, step to enter PARKING - Front parking pad (2 vehicles) -- THE LOCATION -- - 2 miles to Marie Selby Botanical Gardens - 3 miles to Bayfront Park - 5 miles to St. Armands Circle - 6 miles to Lido Key Beach - 7 miles to Mote Marine Laboratory & The John & Mable Ringling Museum of Art - 7 miles to Sarasota Bradenton International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $150 fee (+ fees & taxes) - No events, parties, or large gatherings - Per Florida guidelines, guests must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe quiet hours after 11:00 PM ADDITIONAL INFORMATION - This single-story home requires a step to enter - A long-term tenant lives on-site behind the cottage. They may be present during your stay - Your safety matters. This property features 1 exterior security camera located in the doorbell, facing outward toward the front entrance. It does not look into any interior spaces. The camera records video and sound when activated by motion

Sleeps 8 • Private Pool • Dog Friendly • Balcony

Sarasota, FL, US
3 Bedrooms 6 Guests
Aug 17 - 19
$152 night

This 3-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Private Pool • Outdoor Patio • Private Balcony • Board & Card Games • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Beds • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Washer & Dryer • Dog Friendly • Ample Parking Welcome to your Sarasota getaway! This beautifully appointed home offers the perfect blend of comfort, style, and convenience for families and groups alike. With 3 spacious bedrooms, 2.5 bathrooms, and room to accommodate up to 6 guests, you’ll have plenty of space to relax, unwind, and make unforgettable memories. Step inside to enjoy bright, airy living spaces, a fully equipped kitchen, and cozy gathering areas perfect for movie nights or game time. Outside, soak up Florida’s sunshine while enjoying the backyard retreat, or take a short drive to explore Sarasota’s world-famous beaches, cultural attractions, and dining scene. Whether you’re planning a family vacation, a couples’ getaway, or a trip with friends, this Sarasota gem is designed for comfort and connection. MAIN SPACES OF THE HOME: – 3 BEDROOMS & 2.5 BATHROOMS – BEDROOM 1: * 2 Twin-sized Bed * Nightstand and Lamp * Ceiling Fan * Ensuite Bathroom BEDROOM 2: * King-sized Bed * Smart TV * Nightstand and Lamps * Ceiling Fan * Direct Outdoor Access * Ensuite Bathroom BEDROOM 3: * Queen-sized Bed * Smart TV * Nightstand and Lamp * Direct Balcony Access – 2.5 BATHROOMS – * Ensuite Bathroom with Walk-in Shower * Ensuite Bathroom with Walk-in Shower * Half Bathroom – CHEF’S KITCHEN – * Fully Stocked * High-end Appliances * Large Refrigerator * Ample Cabinetry * Large Island w/ High Seating * Coffee Maker: Drip & Keurig – LIVING ROOM – * Smart TV * Large Plush Sofa + Seating * Expansive Windows * Board & Card Games * Ceiling Fan * Open Floor Plan The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Check-in is at 4pm Check-out is at 10am - Up to 2 dogs are allowed for $125 per stay, no cats please. We kindly ask that your dog is crate trained and that you pick up after your dog. - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - An exterior camera is installed solely to monitor our cleaning team for quality and security purposes. - Parking in the driveway for 8 cars max. Street parking allowed: NO - If you’re interested in a long-term stay, please reach out to inquire about availability. - Guests must be 21 years or older to book this property. GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out.

Casa Tranquilo

Sarasota, FL, US
3 Bedrooms 8 Guests
Aug 17 - 24
$212 night

Welcome to Casa Tranquilo! Book this beautifully renovated 3-bedroom, 2-bath modern home in an upscale Sarasota neighborhood, just 11 minutes from Siesta Key Beach. Ideally located near Siesta Key Village, Trader Joe’s, bike rentals, and local favorites like Rico’s Pizza & Pasta, it’s the perfect spot for both relaxation and convenience. LOCATION HIGHLIGHTS: - Upscale Sarasota neighborhood - Just 11 minutes to Siesta Key Beach - 3.5 miles to Siesta Key Village for dining, shopping & nightlife - Close to Trader Joe’s, bike rentals, and casual dining like Rico’s Pizza & Pasta PROPERTY FEATURES: - 3 bedroom/ 2 bathroom private home (1204 sq ft) - Pet friendly (reach out to us about approval) - Spacious driveway, private washer and dryer - Private fenced in side yard with loungers and outdoor furniture and grill - Dedicated WIFI and cable provided LIVING ROOM: - Coastal-inspired décor with a beachy theme - Two sofas (one is a full-size sleeper) - Large flat-screen TV with Xfinity WiFi & cable KITCHEN AND DINING: - Open kitchen with stainless steel appliances - Natural stone countertops - Dining table for 4, plus 2 more at the breakfast bar BEDROOMS AND BATHROOMS: - Master bedroom: king bed with smart TV - Guest bedroom #1: king bed with laundry room access - Guest bedroom #2: queen bed - Master ensuite bathroom: walk in shower - Guest bathroom: tub/shower combo EXTRA PERKS: - Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels LOCAL FAVORITES: - Siesta Key Beach – powdery white sands & turquoise waters - Siesta Key Village – live music, shopping & dining - Trader Joe’s for convenient grocery runs - Rico’s Pizza & Pasta – local favorite casual spot - Easy access to bike rentals for exploring the area IMPORTANT INFO: - Minimum 7-night stay required - City of Sarasota Certificate of Registration #VR25-00009 - Non-smoking home - Dogs allowed with prior approval & fee (no cats) YOUR DREAM SIESTA KEY GETAWAY AWAITS - BOOK NOW AND LET THE ISLAND’S BEAUTY DO THE REST! All pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs. IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

6 Mi to Siesta Beach! Extended Getaway w/ Pool

Sarasota, FL, US
3 Bedrooms 8 Guests
Aug 17 - Sep 16
$229 night

4 Mi to Downtown Sarasota | Bring Your Pups | Garage Parking | Lounge Seating | BBQ Grill Embrace the laid-back Florida lifestyle at this Sarasota vacation rental, offering a prime location and essentials for a slower, sunnier daily rhythm! Start your day with a refreshing pool dip, then hit the waves at Siesta Key Beach or shop around at St. Armands Circle. When it’s time to unwind, cook a comforting meal in your own space or enjoy a nightcap out on the patio. Secure your extended escape! -- THE PROPERTY -- OUTDOOR LIVING - Private pool (unheated) - Adirondack chairs, lounge chairs w/ umbrella - Grill (propane provided) INDOOR LIVING - Open-concept layout, modern furnishings - Dedicated workspace - 4 Smart TVs - 6-person dining area - Washer & dryer KITCHEN - Microwave, refrigerator, stove/oven, dishwasher - Stainless steel appliances, granite countertops - Cooking basics, dishware & flatware - Keurig coffee maker (coffee provided) - Air fryer ACCESSIBILITY - Single-story home, 2 small steps to enter PARKING - Garage (2 vehicles) - Driveway (2 vehicles) - No street parking -- THE LOCATION -- - Residential neighborhood near golf, dining & everyday essentials - 2 miles to Westfield Siesta Key area: movie theater, restaurants, grocery stores - 4 miles to Marie Selby Botanical Gardens - Under 5 miles to Bayfront Park - 7 miles to St. Armands Circle - 9 miles to The John & Mable Ringling Museum of Art -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $450 fee (+ fees & taxes, dogs only, 2 pets max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe quiet hours from 10:00 PM to 8:00 AM ADDITIONAL INFORMATION - Single-story home, 2 small steps to enter - Long-term renter on-site (separate unit, mother-in-law suite) SECURITY CAMERA INFORMATION - 1 exterior device - Location: doorbell - Coverage: front entrance

Sarasota House w/ Private Pool - 4 Mi to Beach!

Sarasota, FL, US
2 Bedrooms 4 Guests
Aug 17 - 24
$236 night

Whether you're looking to spend time by the pool or at the beach, 'Siesta Jewel’ is perfect for travelers on a memorable Floridian adventure and snowbirds seeking to escape the winter! Lounge in the home’s pleasant lanai or prepare a delicious meal on the patio’s gas grill. This 2-bedroom, 2-bathroom Sarasota vacation rental is also located in a quiet neighborhood just minutes away from golf courses, Marie Selby Botanical Gardens, Bayfront Park, and some of America's most beautiful beaches! -- THE PROPERTY -- Lanai | Gas Grill | Quiet Neighborhood | 4 Mi to Marie Selby Botanical Gardens | Near Golf Bedroom 1: King Bed | Bedroom 2: King Bed OUTDOOR LIVING: Private outdoor pool, pool toys, lounge seating, patio, beach chairs/umbrellas, boogie boards INDOOR LIVING: Flat-screen TV w/ cable, leather sofa, ceiling fans, en-suite bathroom KITCHEN: Stove/oven, refrigerator, microwave, dishwasher, dishware/flatware, cooking basics, coffee maker, Crockpot, toaster, blender, expansive counters, breakfast bar GENERAL: Free WiFi, central air conditioning, towels/linens, washer/dryer, laundry detergent, hair dryer, trash bags/paper towels, keyless entry ACCESSIBILITY: Single-story home, 1 step to enter FAQ: Quiet hours starting at 9:00 PM, 2 exterior security cameras (facing out), optional nightly pool heat fee (paid pre-trip, applied to entire stay) PARKING: Garage (2 vehicles), driveway (2 vehicles), street parking (first-come, first-served) -- THE LOCATION -- SAND & SUN: Public Beach Access (4 miles), Crescent Beach (5 miles), Sarasota Beach (6 miles), Siesta Beach (6 miles), Indian Beach Park (7 miles), Lido Key Beach (8 miles) ATTRACTIONS: Marie Selby Botanical Gardens Downtown Sarasota (4 miles), Bayfront Park (4 miles), Mote Marine Laboratory & Aquarium (8 miles) GOLF: Village Green Golf Club (1 mile), The Palms Golf Club at Forest Lakes (2 miles), Bobby Jones Golf Club (5 miles), The Highlands Golf Course (7 miles), The Groves Golf Course (7 miles) DAY TRIPS: Walt Disney World Resort (119 miles), Universal Studios Florida (126 miles) AIRPORT: Sarasota Bradenton International Airport (8 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story home requires 1 step to enter - NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the street, and a Ring spotlight exterior security camera located on the garage facing the street. The cameras do not look into any interior spaces. The doorbell camera records video and sound for 30 seconds when motion is detected by the device. The spotlight camera will turn on the spotlights and walkway lights for 3 minutes when activated by motion; it will also record video and sound for 60 seconds - NOTE: Please observe quiet hours after 9:00 PM - NOTE: There is an optional pool heat fee of $35/night (+ fees & taxes, paid pre-trip, applied to entire stay)

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Vacation Rentals Near Sarasota

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