Large group vacation rentals in South Sarasota, FL

Looking for a tropical escape? This cozy cottage is perfect for you! A short drive or bike ride will be all that separates you from Siesta Key and some of the best beaches in West Florida. You'll be within walking distance of fantastic local restaurants and only 3 miles south of downtown Sarasota where you can find excellent museums and parks. With 2 bedrooms and 2 baths, this lovely craftsman-constructed vacation rental will meet all your needs for a sunny weekend stay with friends or family! -- THE PROPERTY -- Free WiFi | Backyard w/ Patio | Private Shed for Bike Storage Bedroom 1: Queen Bed | Bedroom 2: Full Bed w/ Full Trundle INDOOR LIVING: Smart TV, wood-burning fireplace, 4-person high-top table KITCHEN: Fully equipped, blender, coffeemaker, cooking basics, dishware/flatware, hot water pot, ice maker, microwave GENERAL: Air conditioning, washer/dryer, linens, towels, hair dryer, hangers FAQ: 3 stairs required for access, suitable for children & elderly guests PARKING: Driveway (2 vehicles) -- THE LOCATION -- BEACHES + PARKS: Bayfront Park (3.7 miles), Siesta Key Beach (5.2 miles), Lido Key Beach (6.9 miles), South Lido County Park (7.6 miles), Oscar Scherer State Park (9.7 miles), Myakka River State Park (21.6 miles) EAT + DRINK: Oasis Cafe (0.1 miles), Demetrio's Restaurant and Pizza (0.3 miles), Walt's Fish Market Restaurant (0.5 miles), Cafe Baci (0.5 miles), Fleming's Prime Steakhouse and Wine Bar (0.9 miles), Shakespeare's Craft Beer and Gastro Pub (1.1 miles), Siesta Key Oyster Bar (4.6 miles) SARASOTA MUST-SEES: Marie Selby Botanical Gardens (3.6 miles), The Ringling Beach House (5.5 miles), Sarasota Jungle Gardens (6.5 miles), Mote Marine Laboratory and Aquarium (7.7 miles), The John and Mable Ringling Museum of Art (7.9 miles) AIRPORT: Sarasota-Bradenton International Airport (8.4 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: The property requires 3 stairs to access and may be difficult for guests with limited mobility

Just beyond the stunning island of Siesta Key, known for brilliant white powder sand and turquoise waters this quaint and cozy home waits to welcome you. Siesta Key is a virtual island paradise but this prime location is also only 10 min from Sarasota village and the number one beach in the USA. A perfect setting for a weekend getaway or even an extended stay. The home is situated in the midst of towering oak trees that provide both ambiance and ample shade while still affording guest the opportunity to sunbathe. Extensive remodeling was completed just a month ago including beautiful plank flooring throughout and stainless steel appliances plus granite countertops in the lovely kitchen. Both bathrooms were also part of the remodeled including tile showers and glass doors in the primary bedroom. Remote controlled ceiling fans throughout make sure you stay cool and comfortable. You’ll enjoy a respite in the private back yard. Walk to Publix or one of the five great restaurants, including Walt’s seafood restaurants (BEST IN SARASOTA). Siesta Village offers shopping, more top-rated restaurants, entertainments, a vibrant nightlife and coffee shops There are any number of special events held throughout the year on the Key’s famous beaches. This is truly a paradise to enjoy and share with family, friends and love ones. Demand is high and calendars are filling fast so book your stay today! NO SMOKING, NO PETS. BEACH CHAIRS AVAILABLE. BEACH UMBRELLA AVAILABLE. BEACH TOWELS. If you are staying longer and in need for more cleaning services, please reach out to the manager. Additional fees may apply. **Please note our maintenance guy will be there on every Tuesdays to take the trash out. ** MAX 6 people allowed to occupy the residence No Parking of Jet Skis No Parking of RV Trailers Hosted by RedAwning Vacation Rentals, over 1,000,000 Guests Served Welcome to RedAwning, a whole new way to travel. We make staying in a unique home or apartment easier than staying at a hotel. By partnering with local hosts throughout North America, we provide you with the broadest collection of homes in the most destinations. Every stay includes our experienced 24/7 customer assistance, our free mobile app, and accidental damage protection for your trip with no security deposits. Wherever you want to go, RedAwning is here to make your journey easier! Want your own property to be included here and in the RedAwning Collection? Join Us and we will instantly promote your property everywhere guests shop for travel.

This 3-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Private Pool • Fire Pit • Outdoor Patio/Dining • BBQ Grill • Game House: Ping Pong Table, Basketball Hoops, 1 Child and 2 Adult Bikes! • Den w/ Smart TV & Dedicated Workspace • Fully Stocked Kitchen • Drip Coffee Maker • Plush Beds • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Dog Friendly • Ample Parking • Washer & Dryer Pack your bags and bring the whole crew—this 3-bedroom, 2-bathroom home sleeps up to 8 guests and is designed for both relaxation and fun. Start your mornings with a splash in the private pool, lounge on the patio, or wind down by the firepit under the stars. Feeling playful? Head to the indoor game room for a round of ping pong or grab the bikes and cruise around the neighborhood like a local. Conveniently located, our home offers easy access to nearby attractions, shopping, and dining options. Whether you’re here for sunny pool days, cozy nights by the fire, or friendly game competitions, this home has all the right vibes for an unforgettable Sarasota getaway! MAIN SPACES OF THE HOME: – 3 BEDROOMS & 2 BATHROOMS– BEDROOM 1: * King-sized Bed * Smart TV * Nightstand and Lamps * Dedicated Workspace * Cozy Seating * Ensuite Bathroom BEDROOM 2: * Queen-sized Bed * Nightstand and Lamp * Ceiling Fan * Closet BEDROOM 3: * King-sized Bed * Nightstand and Lamp * Dresser w/ Mirror * Ceiling Fan – 2 BATHROOMS – * Ensuite Bathroom with Walk-in Shower * Full Bathroom with Shower/Tub Combo – CHEF’S KITCHEN – * Fully Stocked * High-end Appliances * Large Refrigerator * Ample Cabinetry & Cooking Space * Coffee Maker: Drip – LIVING ROOM – * Smart TV * Sofa Bed (Queen) * Ceiling Fan * Open Floor Plan – GAME ROOM – * Ping Pong Table * Basketball Hoops * 1 Child & 2 Adult Bikes * Full-sized Fridge * Beach Essentials: Pool Toys, Coolers, and Beach Gear – OUTDOOR FUN & AMENITIES – * Private Pool * Fire Pit * Outdoor Patio/Dining * BBQ Grill 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. - Parking in the driveway with a carport for 5 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 25 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.

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

Canal Views & Picturesque Sunsets | 5 Mi to Siesta Key | Snowbirds & Remote Workers Welcome Whether you're seeking a peaceful escape or an adventurous getaway, you'll find that this 5-bedroom, 3-bath vacation rental has everything you need for your extended stay in Sarasota. Take a refreshing dip in the private pool, make sandcastles on nearby beaches, and enjoy an afternoon picnic at Bayfront Park. As the sun sets, come home for dinner and a cozy movie night with your crew. Book today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed, 1 full sleeper sofa - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed - Bedroom 4: 1 twin bed w/ 1 twin trundle - Bedroom 5: 1 queen sleeper sofa MAIN FEATURES - Smart TV - Dining tables - Private boat dock - Screened-in lanai w/ private pool (not heated) - Spacious yard KITCHEN - Refrigerator, stove/oven, dishwasher, microwave - Drip coffee maker (bring your own coffee) - Cooking basics, dishware/flatware GENERAL - Free WiFi - Central A/C & heating, ceiling fans - Linens & towels, trash bags & paper towels - Complimentary toiletries - Washer/dryer FAQ - 2 exterior security cameras (facing out) - Quiet hours (after 11:00 PM) ACCESSIBILITY - Single-story home, 1 small step required to enter PARKING - Garage (1 vehicle) - Driveway (2 vehicles) -- THE LOCATION -- - 4 miles to Siesta Beach, 9 miles to Lido Key Beach, 13 miles to Nokomis Public Beach & 15 miles to Venice Beach - 5 miles to Sarasota Art Museum & 10 miles to The John and Mable Ringling Museum of Art - 6 miles to Bayfront Park - 9 miles to Sarasota Jungle Gardens - 10 miles to Mote Marine Laboratory & Aquarium - 10 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/ $75 fee (+ fees & taxes, max 1 pet) - 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 - Please observe quiet hours after 11:00 PM ADDITIONAL INFORMATION - Your safety matters. This property features 2 exterior security cameras. Camera 1 is on the front of the house facing the entryway, and camera 2 is on the back of the house facing the lanai and backyard. The cameras are outward facing and do not look into any interior spaces. They actively record video and audio while guests are in the residence - This single-story home requires 1 small step to enter

🌴 Casamigos | Heated Saltwater Pool & Tiki Bar 💖 Why You’ll Love This Home Experience island elegance at Casamigos, a tropical oasis designed for memorable gatherings. From a private heated saltwater pool to an authentic 8-seat tiki bar, every detail invites you to unwind in style. This upscale retreat blends vibrant West Indies charm with modern luxury—ideal for creating lasting vacation memories. 👨‍👩‍👧 Perfect For Multi-generational families, friend groups, and anyone seeking a stylish, spacious getaway near Siesta Key’s best beaches and dining. 🎞️ Imagine This Imagine waking to the soft Florida sun filtering through towering palms as you step into an airy living room with 12-foot ceilings and cool coastal breezes. Hear the gentle splash of the heated pool just beyond sliding glass doors, where the scent of bougainvillea mingles with fresh breakfast from the gourmet kitchen. In the afternoon, enjoy a fresh panini from the provided press and unwind with a glass of wine from the wine fridge. In the evening, gather with friends at the tiki bar under twinkling lights, sharing cocktails and laughter surrounded by lush tropical blooms and complete privacy. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, TV • Bedroom 2: King Bed, Hall Bath, TV • Bedroom 3: King Bed, Hall Bath, TV • Bedroom 4: King Bed, Hall Bath, TV • Bedroom 5: 2 Twin Beds, Shared Bath 📍 Explore the Area • 3.4 Miles to Siesta Key Village, Full of Shops, Cafes, and Nightlife • 4.5 Miles to Siesta Key Beach, Famous for its Powdery White Sand • 2.2 Miles to Downtown Sarasota, Dining, Shopping, Parks • 5.5 Miles to Lido Key’s Beaches and Restaurants ⌛ Don’t wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection. 📝 Need to Know: Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights. Free high-speed WiFi included. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. Please inquire if any guests require stair-free access. This property is registered as a vacation rental with the City of Sarasota with a Registration Number of VR25-00068 Due to City of Sarasota vacation rental code, this property must be rented once during a seven (7) day period and have a maximum occupancy of 10 guests. The primary guest making the reservation must be at least 26 years of age.

🌴 Ventana Rosa | Heated Pool + Lush Tropical Outdoor Living 💖 Why You’ll Love This Home Wrapped in tropical foliage and designer touches, Ventana Rosa is a beautifully renovated Sarasota retreat with a private heated pool, lush outdoor space, and thoughtfully styled interiors. Just minutes from Siesta Key Beach, it offers a seamless indoor-outdoor flow for families or groups to reconnect and unwind in comfort. 👨‍👩‍👧 Perfect For Ideal for families, friend groups, and remote work escapes looking for a serene, upscale home base with easy access to Siesta Key and downtown Sarasota. 🎞️ Imagine This Start your morning on the shaded poolside terrace, sunlight flickering through palm fronds. The kids splash in the heated pool while you prepare brunch in the gourmet kitchen stocked with modern appliances and bright quartz counters. After a beach day just minutes away, rinse off in the outdoor shower, fire up the gas grill for dinner, and share stories beneath string lights in your private tropical hideaway. End the evening curled up on the sofa, planning tomorrow’s adventures on Florida’s Gulf Coast. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, En-Suite Bath with Walk-In Shower, TV • Bedroom 2: King Bed, Shared Bath, TV • Bedroom 3: Queen Bed + 2 Twin Beds, Shared Bath, TV • Living Room: Sleeper Sofa (Queen), Ground Floor 📍 Explore the Area • 1.7 miles to Siesta Key Beach – world-famous quartz sand and turquoise water • 1.5 miles to Siesta Key Village – boutiques, dining, nightlife • 4.8 miles to Downtown Sarasota – arts, shopping, and cultural attractions • Surrounded by walkable neighborhoods, local parks, and island energy ⌛ Don’t Wait—This Home Books Fast Your stay includes peace of mind with our CottageClean™ program, featuring a 6-hour deep clean and 35-point inspection before your arrival. Starter packs of kitchen and toiletry essentials are included for a seamless first few nights. Free High-Speed WiFi is provided throughout the home. 📝 Need to Know: This is a single level home. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. This property is registered as a vacation rental with the City of Sarasota with Registration Number VR25-00069.

☀️ Siesta Sun Oasis | Private Pool, Walk to Siesta Key Beach, Game Room & Large Backyard Court 💖 Why You’ll Love This Home Siesta Sun Oasis offers a spacious island retreat designed for gathering, relaxing, and enjoying time outdoors. With five bedrooms and a large backyard built for recreation, this home makes it easy to balance beach days with time spent at home. A complimentary 6-passenger golf cart is included with bookings through November 1st and ready upon arrival, courtesy of Robin Hood Rentals, making it easy to explore Siesta Key’s beaches, shops, and restaurants. The private pool and oversized concrete court create a setting where everyone can find their favorite way to unwind, from poolside lounging to friendly games of pickleball or soccer. Inside, the home blends comfort and functionality with generous living spaces and a well-equipped kitchen featuring LG appliances, a wine cooler, and a combination microwave, air fryer, and oven for easy meals and entertaining. Siesta Sun Oasis provides the space to enjoy every part of your stay. 👨‍👩‍👧 Perfect For Families, multi-generational groups, or friends looking for a spacious Siesta Key stay with outdoor activities, poolside relaxation, and room for everyone to spread out. 🎞️ Imagine This Start the day outside as the morning sun fills the backyard. Plan the day around a quick trip to Siesta Key Beach before returning home to cool off in the private pool. In the afternoon, challenge friends to a game on the backyard court, perfect for pickleball, soccer, or casual outdoor play while others relax by the pool or gather inside around the pool table. As evening settles in, the backyard becomes the heart of the home. Start up the grill, share stories from the day, and enjoy the warm island air before retreating indoors to comfortable bedrooms across the home. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, TV • Bedroom 2: King Bed, TV • Bedroom 3: Queen Bed, TV • Bedroom 4: Queen Bed, Ensuite Jack and Jill Bath, TV • Bedroom 5: Queen Bed, Ensuite Jack and Jill Bath, TV • Office: Sleeper Sofa (Connected to the Primary Suite) 📍 Explore the Area • 0.5 Miles to Siesta Key Beach – Powdery White Sand and Gulf Swimming • 1.5 Miles to Siesta Key Village – Restaurants, Coffee Shops, and Island Boutiques • 1.6 Miles to Crescent Beach – A Scenic Stretch of Shoreline with Calm Waters • 6.0 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Dining • 9.2 Miles to St. Armands Circle – Upscale Shopping and Restaurants ⌛ Book Today: Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection. 🔎 Need to Know: Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. We happily welcome one small dog (up to 25 lbs) with a $250 pet fee—breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup’s stay just as wonderful as yours.

Welcome to Harbor Towers Yacht & Racquet Club 2nd FL Renovated Unit! Experience the best of Siesta Key from this beautifully renovated, second-floor sanctuary. Nestled directly on the Intracoastal Waterway, this spacious 3-bedroom condo combines modern interior luxury with the high-end amenities of a premier yacht and racquet club. Whether you’re catching the sunrise over the marina or taking a 15-minute stroll to the world-famous white sands of Siesta Key Beach, paradise is right at your doorstep. RESORT-STYLE AMENITIES - Aquatic Fun: Two heated swimming pools for year-round relaxation. - Tennis & Fitness: Three professional-grade Har-Tru clay tennis courts, a fully equipped fitness center, and a sauna. - The Marina Life: Beautiful bayfront setting with boat docks, BBQ grilling stations, and a vibrant clubhouse. - Easy Island Travel: The Siesta Key Trolley stops right outside, whisking you away to the Village for dining and live music—no car needed! PROPERTY HIGHLIGHTS - Spacious 3BR Layout: Over 1,500 sq. ft. of renovated living space, perfect for families or groups. - Chef’s Kitchen: Fully equipped for vacation meal-prep with a large breakfast bar seating four. - Enclosed Balcony: Accessible from the living room, offering a cozy spot to unwind after a day in the sun. - Laundry & Tech: Private in-unit washer/dryer, dedicated high-speed WiFi, and cable TV in every bedroom. BEDROOMS & BATHROOMS - Master Suite: King bed, corner windows with great light, and an ensuite bath with a spacious walk-in glass shower. - Guest Bedroom 1: Comfortable Queen bed with views of the tranquil front entrance pond. - Guest Bedroom 2 (The Mega-Suite): Features two Queen beds—a rare find that makes this unit perfect for kids or multiple couples. - Guest Bath: Modernized tub/shower combo with sleek glass doors. EXTRA PERKS - Beach Bundle: We provide beach chairs, an umbrella, and fresh towels so you can pack light. - Parking: Includes one assigned parking space. LOCAL FAVORITES: - Siesta Key Beach with powder-white sand and turquoise water - Siesta Key Village restaurants, bars, and boutique shops - Trolley rides to the beach and village hotspots IMPORTANT INFO - Quiet & Pristine: This is a peaceful community with enforced quiet hours. No parties, smoking, or pets (including ESAs) are permitted. - Parking Limits: Strictly one vehicle only. No trailers, oversized vehicles, boats, or motorized scooters/carts allowed per association rules. PARADISE IS CALLING - ANSWER WITH A RESERVATION ON BEAUTIFUL SIESTA KEY! Please note, each unit is only allowed 1 parking spot. Starting June 1st, the complex has scheduled a roof repair. They are expecting to be done in 4-5 weeks (weather permitting). Crane will be up front. Carport repairs will take place starting June 8, 2026. Please use caution around work areas. Thanks for your understanding. Xplorie Activities and Airport Transportation -One complimentary activity per day: bike rental, kayak rental, dolphin cruise tour, or Ringling Museum admission -Limited to one person per day; additional guests can join for a fee -Round-trip airport transportation included for up to 3 passengers from SRQ or TPA with advance reservation (driver tip appreciated) -Activities subject to availability and change; non-cumulative and non-transferable -Not available for stays of 25 nights or longer IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Harbor Towers 530 by Tropical Sands Accommodations Welcome to Harbor Towers 530, an elevated two-bedroom, two-bath Siesta Key vacation rental located in the gated Harbor Towers Yacht and Racquet Club on Midnight Pass Road. Perched on an upper floor with sweeping waterfront views of the Intracoastal Waterway, tropical palms, and sparkling pool below, this refined residence offers a sophisticated island retreat just minutes from Crescent Beach. With a 13-night minimum stay requirement, this condo is ideal for extended seasonal getaways and luxury snowbird escapes. Highlights • 2 Bedrooms / 2 Bathrooms • 2 King beds • Private balcony with panoramic water views • Upper-floor residence • 13-night minimum stay community • Gated waterfront property • Two heated pools • Three Har-Tru tennis courts • 40-slip marina on the Intracoastal Waterway • Fitness center and sauna Harbor Towers is one of the most desirable waterfront communities on Siesta Key, known for its upscale atmosphere and loyal returning guests. The property features two heated pools surrounded by lush tropical landscaping, three Har-Tru tennis courts, and a 40-slip marina along the Intracoastal Waterway. From your private balcony in Unit 530, take in breathtaking panoramic views stretching across palm lined grounds, the marina, and shimmering waters beyond. Whether enjoying sunrise coffee or evening cocktails, the elevated vantage point makes every moment feel special. Unit 530 offers an elegant open concept layout with refined finishes and an abundance of natural light. The living area features plush seating, sophisticated decor, and large windows that frame stunning water views. Sliding glass doors open to the private balcony, creating seamless indoor and outdoor living. The gourmet kitchen is beautifully appointed with rich dark cabinetry, granite countertops, stainless steel appliances, and plenty prep space. The layout flows effortlessly into the dining area, where meals are enjoyed against a backdrop of panoramic views. The primary bedroom features a king bed, serene coastal tones, and expansive windows showcasing water views. The private ensuite bathroom includes updated finishes and a spacious shower, creating a spa like retreat for extended stays. The second bedroom also offers a king bed, making this layout ideal for two couples or guests seeking equal comfort. A full hallway bathroom is conveniently located near the guest bedroom and main living area. Both bedrooms are designed for relaxation, offering generous storage and calming spaces to unwind after days spent at Crescent Beach. Room Details • Primary Bedroom: King bed and ensuite bathroom • Second Bedroom: King bed • Hallway Bathroom: Full bath Harbor Towers 530 is located within a 13-night minimum stay community, providing a quieter, more residential atmosphere that is especially appealing to seasonal guests. The beautifully maintained grounds offer walking paths, waterfront views, and easy access to the pools, tennis courts, and marina. Conveniently located near Crescent Beach and just a short drive to Siesta Key Village dining and shopping, this residence combines peaceful waterfront living with close proximity to the island’s top attractions. If you are searching for a Siesta Key condo rental with panoramic water views, two king suites, and resort style amenities in a gated waterfront setting, Harbor Towers 530 by Tropical Sands Accommodations delivers an elevated extended stay experience. Enjoy sunrise views from your balcony, relax by the pools, and embrace the refined island lifestyle that brings guests back to Harbor Towers year after year. Secure your dates today and experience the best of Siesta Key living.

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.

🌴 The Sun Dial | Waterfront Pool Home + Walk to Beach 💖 Why You’ll Love This Home Nestled on the peaceful canals of Siesta Key, The Sun Dial offers the perfect fusion of luxury, privacy, and adventure. From sunrise coffee on your private balcony to kayaking the calm waterways at sunset, this home was made for unforgettable moments. With a private heated pool, spacious layout, and just 1 mile from world-famous Siesta Key Beach, every detail is designed for comfort, style, and coastal charm. 👨‍👩‍👧 Perfect For Ideal for multi-generational families, couples traveling together, or groups seeking high-end comfort with waterfront access. 🎞️ Imagine This... You wake to the glow of the morning sun reflecting off the water, brewing coffee in your private master suite kitchenette before stepping onto the balcony to watch kayakers drift by. The breeze is warm, the canal still. Later, everyone gathers in the open-concept kitchen and living area—kids splash in the large private pool while adults sip mimosas under swaying palms. Maybe someone spots the custom sun dial in the garden and snaps a photo—it’s little touches like that which make this place feel different. In the afternoon, you launch a kayak and explore the serene backwater channels, or take the short stroll to Siesta Key Beach (1 mile) for an ocean swim. As the day winds down, the group heads to Siesta Key Village (1.8 miles) for fresh seafood and live music. Back home, the laughter continues under starlit skies on your private lanai. The Sun Dial isn’t just a place to stay—it’s part of the story you’ll tell. 🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, Top Floor, TV, Private Balcony, Kitchenette • Bedroom 2: King Bed + Twin Bunk Bed, Shared Bath, Main Floor, TV • Bedroom 3: King Bed, Ensuite Bath, Main Floor, TV • Bedroom 4: King Bed, Shared Bath, Main Floor, TV • Bonus Space: Queen Sleeper Sofa – Living Room 📍 Explore the Area • 1.0 mile to Siesta Key Beach (walkable via shaded neighborhood roads) • 1.8 miles to Siesta Key Village – shops, restaurants, nightlife • Canal access on-site – 2 kayaks provided • Watch sunsets, explore barrier island nature, or walk to dinner by the sea ⌛ Don’t Miss Out This luxury home books quickly, especially in high season. Your stay includes peace of mind with our CottageClean™ program: a six-hour deep clean and a 35-point inspection before every guest arrival—so you can vacation worry-free from the moment you arrive. 📝 Need to Know - There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th. Exterior security cameras are installed at the front door for security purposes only. No cameras are located inside the home or in private guest areas.

Escape to Siesta Key’s Hidden Treasure – A Peaceful, Private Island Retreat Welcome to Siesta Key’s Hidden Treasure, a delightful, tranquil escape offering the perfect balance of comfort and luxury. This charming property features a spacious 2-bedroom, 2-bathroom main house and a detached 2-bedroom, 1-bathroom Casita, ideal for larger groups or families looking for both shared and private spaces. Whether you’re seeking relaxation or adventure, Hidden Treasure has everything you need for an unforgettable getaway. Charming and Comfortable Living Spaces Step inside the main house, where you’ll find a bright and cheerful atmosphere designed to make you feel right at home. The main bedroom serves as a peaceful retreat, complete with a luxurious ensuite bath featuring double sinks, an opulent shower, and a seated dressing vanity. The detached Casita off the screened patio provides a cozy, private getaway with a king bedroom, a twin bedroom with two beds, and a shared full bath. With 2 king beds, 1 queen bed, and 2 twin beds, the home comfortably accommodates up to 8 guests, perfect for families or friends. Fresh linens are provided for your convenience. Outdoor Paradise Awaits The heart of this home lies in the screened pool and patio area, a true backyard oasis. Step through the sliding glass doors into a tropical paradise, featuring a private heated saltwater pool, a hot tub, multiple dining areas, and an elevated sun deck perfect for soaking up the sun. Relax poolside in the spacious courtyard, fire up the grill, or enjoy a meal while basking in the gorgeous island weather. As the day winds down, gather around the fire table for breathtaking sunset views. The Banyan tree with its sprawling roots stands as the centerpiece of the lush, tropical landscape, offering an enchanting atmosphere. Fully Equipped for a Seamless Stay The home provides all the essentials to ensure a stress-free vacation. Brew your favorite coffee using the regular or Keurig coffee maker, prepare meals with the fully equipped kitchen, and enjoy the convenience of a dishwasher, washer/dryer, and other amenities for a hassle-free stay. Ideal Location for Siesta Key Adventure Hidden Treasure offers the perfect location for enjoying all that Siesta Key has to offer. In just minutes, you can sink your toes into the powdery white sands of Siesta Key Beach, renowned for its beauty and serenity. Take a scenic stroll or bike ride to the charming Siesta Key Village, where you’ll find a variety of dining, shopping, and entertainment options. Book Your Escape Today Whether you’re lounging by the pool, exploring the nearby beach, or simply enjoying quality time with loved ones, Hidden Treasure is the perfect place to create lasting memories. Book your stay today and experience the ultimate Siesta Key getaway, where relaxation, comfort, and natural beauty come together. Exclusive Amenities Include: • Private Screened Saltwater Heated Pool • Private Hot Tub • 10 Minute Walk to Siesta Key Village • 15 Minute Walk to Siesta Key Beach • 2 Bedroom Detached Private Guest Quarters • 4 Bedrooms, 3 Full Baths (1 Master Bedroom) • 2 King Bed, 1 Queen Beds, 2 Twin Beds (Sleeps 8) with linens provided • Sun Deck • Outdoor Dining & Lounge area • Private Garage • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes • Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes • Beach Towels, Chairs, Cooler, & Caddy Provided • Free WiFi & 4 HDTV’s • Gas Grill • Enhanced cleaning protocols provided by our CottageClean Team • Island Shuttle Transportation Available Hidden Treasure can accommodate up to 8 guest with a bedding configuration as follows: Main Cottage: • Bedroom # 1: King Bed (1) - Sleeps: 2 • Bedroom # 2: Queen Bed (1) - Sleeps: 2 Private Casita Guest Quarters: • Bedroom # 3: King Bed (1) - Sleeps: 2 • Bedroom # 4: Twin Beds (2) - Sleeps: 2 We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before! PLEASE NOTE: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th.

Pet Friendly w/ Fee | In-Unit Laundry | Close to Golf Courses Experience the best of the Gulf Coast at this 2-bed, 2-bath Sarasota vacation rental! Perfectly situated for long-term travelers and snowbirds, this home offers everything needed for a seamless stay. Spend your mornings strolling through downtown shops or lounging on Siesta Key’s white sands before returning to unwind in your quiet oasis. Whether you’re working remotely or enjoying a winter escape, book today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS- Bedroom 1: 1 queen bed- Bedroom 2: 2 twin beds KITCHEN- Stove/oven, refrigerator, microwave- Keurig coffee maker (coffee provided), steamer/frother- Cooking basics, dishware & flatware- Trash bags/paper towels MAIN FEATURES- Garage movie room w/ Smart TV- Porch w/ seating- Dining table- Desk GENERAL- Central heating & A/C, ceiling fans- Washer/dryer, iron/board- Linens/towels- Complimentary toiletries, hair dryer- Free WiFi- Keyless entry FAQ- 2 exterior security cameras (facing out)- Pet fee (paid pre-trip)- Quiet hours (starting at 11:00 PM) ACCESSIBILITY- Single-story home, 2 exterior steps to access PARKING- Driveway (2-3 vehicles) -- THE LOCATION -- - Quiet, residential neighborhood near Phillippi Creek & Red Bug Slough Preserve- 4-5 miles to Siesta Beach, Turtle Beach & Sarasota Beach- 5 miles to Bayfront Park- 9 miles to The John and Mable Ringling Museum of Art & Sarasota Jungle Gardens- 18 miles to Bradenton- 9 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/ $50 fee (+ fees & taxes, 1 pet 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 starting at 11:00 PM ADDITIONAL INFORMATION- This single-story home requires 2 exterior steps to access- Your safety matters. This property features 2 exterior security cameras: 1 camera is located above the garage facing the driveway, and 1 camera is located on the home facing the garden. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound continuously

Welcome to Harbor Towers 3rd Fl 2 Bedroom Bay View! This beautiful 3rd-floor, 2-bedroom, 2-bath condo at Harbor Towers offers stunning bay views and is just minutes from Siesta Key and Crescent Beach. Guests enjoy resort-style amenities including two pools, Har-Tru tennis courts, a social room with full kitchen and TV, BBQ grills, and a state-of-the-art fitness center. Peak-season stays are typically Saturday to Saturday, but contact us directly for special scheduling requests. LOCATION HIGHLIGHTS: - Direct bayfront setting on the Intracoastal - Quick 2–3 minute drive or 15-minute walk to Siesta Key Beach - Trolley stop just outside the building - Close to Siesta Key Village dining, shopping, and live music - Resort-style gated community with marina views and sunrise scenery - 2 heated swimming pools, 3 clay tennis courts - Clubhouse with grilling station, exercise facility, and sauna PROPERTY FEATURES: - 2 bedroom/ 2 bathroom 3rd fl condo (1152 sq ft) - Stunning bay views - Dedicated WIFI and cable - 1 assigned parking spot - Central AC - Private washer and dryer LIVING ROOM: - Couch doubles as a sofa bed - Big screen TV with cable - Access to enclosed balcony KITCHEN AND DINING: - Updated kitchen with stainless steel appliances and double sinks - Dining table seats 4 BEDROOMS AND BATHROOMS: - Master bedroom: king bed, large windows - Master ensuite bathroom: spacious vanity with walk-in shower - Guest bedroom: two twin beds, closet, access to enclosed balcony - Guest bathroom: tub/shower combo, vanity EXTRA PERKS: - Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. LOCAL FAVORITES: Siesta Key Beach with powder-white sand and turquoise water Siesta Key Village restaurants, bars, and boutique shops Trolley rides to the beach and village hotspots IMPORTANT INFO: - Quiet hours enforced by the community - No parties or smoking allowed. No pets - Only 1 parking spot. Parking restrictions: no trailers, oversized vehicles, boats, or commercial vehicles. No Motorized Carts or Scooters Allowed DON’T WAIT - YOUR IDEAL ESCAPE IS READY AND WAITING FOR YOU! Please note, each unit is only allowed 1 parking spot. Starting June 1st, the complex has scheduled a roof repair. They are expecting to be done in 4-5 weeks (weather permitting). Crane will be up front. Carport repairs will take place starting June 8, 2026. Please use caution around work areas. Thanks for your understanding. Xplorie Activities and Airport Transportation -One complimentary activity per day: bike rental, kayak rental, dolphin cruise tour, or Ringling Museum admission -Limited to one person per day; additional guests can join for a fee -Round-trip airport transportation included for up to 3 passengers from SRQ or TPA with advance reservation (driver tip appreciated) -Activities subject to availability and change; non-cumulative and non-transferable -Not available for stays of 25 nights or longer IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Welcome to the Sunkissed Pool Home! A beautifully renovated 3-bedroom, 2.5-bathroom private residence on Siesta Key. This upscale home offers a luxurious retreat with a private, enclosed swimming pool, where a new heater can be added for a fee. Perfect for up to 6 guests, the home is ideally located for beachgoers and vacationers alike. LOCATION HIGHLIGHTS: - Siesta Key private home just 1.4 miles from Siesta Key Beach & Pavilion - 1.8 miles from Siesta Key Village with shops, dining, and entertainment - Close to local beaches, parks, and attractions PROPERTY FEATURES: - Renovated 3-bedroom, 2.5-bathroom home (1800+ sq ft) - Private, enclosed pool with optional heater (heat fee extra) - Garage fits one small vehicle (height restriction 5’11”) - Security camera outside and pool door alarm for safety - WiFi throughout the home - Private washer and dryer - Dog-friendly with prior approval and fee (no aggressive breeds, barkers, or chewers) LIVING ROOM: - Family room with large reclining sofa, smart TV for streaming - Open layout connecting to pool and kitchen KITCHEN AND DINING: - High-end stainless steel kitchen with island - Fully stocked with dishes, cookware, and small appliances - Dining table seats 6, island bar seats 4 BEDROOMS AND BATHROOMS: - Master Suite: King bed, en-suite bath with soaking tub, direct pool access - Second Bedroom: Queen bed with pool access - Third Bedroom: Queen bed - Two full bathrooms and one half-bath: walk-in shower and tub/shower combo EXTRA PERKS: - Beach accessories included: towels, couple of chairs, umbrella - Electric George Foreman grill available LOCAL FAVORITES: - Minutes from Siesta Key Village shops, restaurants, and nightlife - Quick access to Siesta Key beaches and watersports IMPORTANT INFO - Maximum occupancy 6 guests - Dogs allowed with prior approval (pets not allowed in pool) - Non-smoking property (vaping restricted to outdoor designated areas) ENJOY YOUR STAY AT THIS SERENE AND WELL-APPOINTED HOME, WHERE YOU CAN RELAX IN STYLE AND COMFORT. 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.

Harbor Towers 417 by Tropical Sands Accommodations Welcome to the perfect Gulf Coast retreat at Harbor Towers 417, a beautifully updated Bayfront condominium nestled directly on the Gulf Coast Intracoastal Waterway. This charming fourth-floor residence offers stunning bay views, near Siesta Key’s powdery sands and warm Gulf waters. With two bedrooms and two bathrooms, it provides a serene escape for families or friends seeking relaxation, outdoor activities, and island adventures. Located within the Harbor Towers Yacht and Racquet Club, guests enjoy access to two heated pools, tennis courts, a fitness center, and scenic water views! Highlights • Bay Views • 10-minute walk to Siesta Key Beach • 2 Bedroom / 2 Bathroom • 1 King, 1 Queen, 1 Sleeper sofa • Private screened-in lanai • Two heated pools • Three Community tennis courts and fitness center • Beach chairs • Short walk or trolley ride to Siesta Key Village • 13-night minimum stay community Relax and unwind with two resort style heated pools and scenic water views from the screened-in lanai. Play tennis on the three courts, stay active in the fitness center, or explore Siesta Key’s beaches and village via the free Siesta Key Breeze Trolley right outside your complex. The outdoor grilling patio and water views create a tranquil setting for memorable outdoor meals and relaxing afternoons. The spacious interior boasts a fully equipped kitchen with modern appliances, perfect for preparing meals and snacks. The chic living room with plush seating and a large TV creates a cozy atmosphere for relaxing after a day of beach adventures. The screened-in lanai extends your living space with beautiful views of the bay and a full dining set for outdoor meals. The primary bedroom features a king-sized bed, lovely beach decor, and a modern ensuite bathroom with a walk-in shower. The second bedroom offers a queen-sized bed with an ensuite bathroom featuring a shower and tub combination, accessed via the bedroom and the living area. A sleeper sofa in the living room provides additional sleeping space, supported by a washer and dryer for added convenience. Room Details • Primary Bedroom: King bed, ensuite bathroom with walk-in shower  • Second Bedroom: Queen bed • Living Room: Sleeper sofa Guests enjoy access to a washer and dryer, outdoor seating, and the complex’s outdoor pools and tennis courts. Explore the on site Marina available for use with an additional fee, registration, and documentation. Situated across from Siesta Key Beach and near the village shops, Harbor Towers 417 provides the perfect base for exploring the island and relaxing in style. Book your stay today at Harbor Towers 417 and indulge in a waterfront escape, amenities, and a prime location. Enjoy stunning bay views, beach days, and island adventures in this upscale condo. Reserve your dates now for an unforgettable Gulf Coast vacation! - This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. This property does not allow pets of any kind. 1 car maximum is able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Discover a peaceful waterfront retreat at this ground-floor condo in the gated Siesta Gulf & Bay Bayside community, located on Siesta Key. No neighbors above you, a private screened lanai overlooking a fountain pond and tropical landscaping, and gated private access to Siesta Key Beach, just an 8-minute walk away. Every day of your stay also includes a free activity and round-trip airport transportation through our Xplorie program (details below). This is island living at a slower pace. Sleeps 6: -Master Suite: King bed, private lanai access, en-suite bath with walk-in shower -Guest Bedroom: Two twin beds, dedicated TV -Living Room: Queen sleeper sofa 1,260 sq ft. Ground-floor unit, no stairs, no upstairs neighbors. Kitchen, Living and Dining Fully equipped kitchen with granite countertops and stainless steel appliances. Breakfast bar seats 4. Central AC, ceiling fans, private washer/dryer, high-speed WiFi and cable. Bathrooms -Primary en-suite: Spacious vanity, walk-in shower -Guest bath: Tub/shower combo Resort Amenities -Gated private access to Siesta Key Beach, 8-minute walk -Two heated community pools -Tennis and pickleball courts -Private fishing pier and boardwalks along the Intracoastal Waterway -Community grilling stations -Free Siesta Key Trolley stop nearby for the Village or south-end shops Ideal for: -Small families, especially during summer and spring break, with the king plus twin bedroom setup -Guests who want resort amenities (pools, tennis, pickleball, fishing pier) in a gated community -Beach-goers who want walkable, gated access to Siesta Key Beach -Longer-stay guests who value in-unit laundry and a full kitchen Extra Perks -Beach chairs, umbrella, and towels provided -Driveway parking included (1 parking pass provided; additional passes available for a fee) -Golf carts welcome (must be stored in garage or driveway) Good to Know -No pets allowed, including emotional support animals -Primary guest must be 25 or older; bookings made by guests under 25 will be cancelled without refund -On-site check-in and parking passes required per association rules -Bayside amenities (pools, tennis, pickleball, pier) and private beach access are included. -Garage is accessed weekly by staff for trash removal -No boats, motorcycles, trailers, or oversized vehicles -Xplorie activities and airport transportation are not available for stays of 25 nights or longer Location South End: -Clayton’s Grill -Miguel’s -Captain Curt’s The Village: -Siesta Key Oyster Bar (SKOB) -Daiquiri Deck -Local boutiques and shops FAQs Is this property on Siesta Key? Yes. The condo is located on Siesta Key. Gated private access to Siesta Key Beach is an 8-minute walk from the unit. Is this a ground-floor unit? Yes. No stairs and no upstairs neighbors, which makes for a quieter stay. How many guests does it sleep? Up to 6: a king bed in the primary, two twin beds in the guest room, and a queen sleeper sofa in the living room. What pools and amenities can guests use? Guests have full access to Bayside amenities, including two heated pools, tennis and pickleball courts, and the private fishing pier. Gulf-side pools in the complex are reserved for residents only. Is there parking? Yes. One parking pass is included with driveway parking. Additional passes are available for a fee. Golf carts are welcome and must be stored in the garage or driveway. Are pets allowed? No. This property does not allow pets, including emotional support animals. Is there a minimum age to book? Yes. The primary guest must be 25 or older. Bookings made by guests under 25 will be cancelled without refund. Does this property include free activities and airport transportation? Yes, through our Xplorie program. See details below for activity options and terms. What’s nearby? Clayton’s Grill, Miguel’s, and Captain Curt’s are all on the south end. The Village has Siesta Key Oyster Bar, Daiquiri Deck, and local boutiques, all reachable via the free Siesta Key Trolley. Xplorie Activities and Airport Transportation -One complimentary activity per day: bike rental, kayak rental, dolphin cruise tour, or Ringling Museum admission -Limited to one person per day; additional guests can join for a fee -Round-trip airport transportation included for up to 3 passengers from SRQ or TPA with advance reservation (driver tip appreciated) -Activities subject to availability and change; non-cumulative and non-transferable -Not available for stays of 25 nights or longer This property does not allow Emotional Support Animals in addition to their no pet policy. IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions. Parking passes: 1 parking pass is provided. There is a fee for extra parking passes.

Welcome to Paradise Palms, a freshly updated three-bedroom sanctuary where island peace meets modern comfort. Tucked away in a quiet residential pocket just minutes from the world-famous white sands of Siesta Key Beach, this home offers the perfect blend of privacy and proximity. Featuring a sparkling screened-in pool and two spacious living areas, it’s a premier choice for families or small groups looking to experience the best of the Gulf Coast. The Highlights - Private Screened-In Pool: Your own tropical oasis for sun-soaked afternoons. - Prime Location: Less than 1.5 miles to Siesta Key Beach access. - Recreation Ready: Ping pong and air hockey tables, plus board games, puzzles, and books. - Beach Gear Included: We provide beach chairs and a beach cart to make your shore days effortless. - Open-Concept Living: Two distinct living rooms with vaulted ceilings and skylights. - Al Fresco Living: Screened lanai with BBQ grill, outdoor dining, and lounge seating. The Living Space The interior of Paradise Palms is designed for relaxation. The bright, airy layout features two separate living rooms, offering plenty of space for the group to spread out. One living area serves as a cozy media room with a large flat-screen TV and direct pool access, while the second boasts soaring vaulted ceilings and coastal decor. Perfect for a quiet morning coffee or evening cocktails! The fully equipped kitchen features modern appliances and bar seating for casual snacks. For family dinners, the formal dining area comfortably seats eight, ensuring everyone has a spot at the table. Bedrooms & Bathrooms - Primary Suite: A true retreat featuring a King bed, private sitting area, and an ensuite bathroom with a walk-in shower. Sliding glass doors lead you directly from your bedroom to the pool deck. - Bedroom 2: Features a comfortable Queen bed and easy access to the hall bath. - Bedroom 3: Perfect for kids or additional guests with a Full bed. - Extra Sleeping: A Queen sleeper sofa in the living room provides flexibility for larger groups. Outdoor Oasis - Step through the sliding doors into your private screened-in lanai. Surrounded by lush tropical landscaping, the pool area is designed for the Florida lifestyle. - Fire up the BBQ grill for a poolside cookout, dine at the outdoor table, or challenge the family to a tournament on the ping pong and air hockey table. Essential Amenities - High-Speed Wi-Fi & Smart TVs for streaming. - Full-Sized Washer & Dryer inside the home. - Parking: Space for up to 4 vehicles (No overnight street parking allowed). - Pet Policy: We are dog-friendly with prior approval and fee! The Neighborhood Paradise Palms is situated in a peaceful residential neighborhood. To maintain the tranquility of our community, we ask all guests to observe local noise ordinances and be respectful neighbors. You are just a short drive or bike ride away from the vibrant Siesta Key Village, local boutiques, and the breathtaking sunset views of the Gulf. Other information: - No smoking property - Pool heat extra - reach out for details. - No parties or large gatherings - This home is in a quiet residential neighborhood. We kindly ask that all guests treat the home and surrounding community with the same care and respect as they would their own. - Per Sarasota ordinance, this rental is limited to 1 rental per 30 day period. Ready to soak up the sun? Book your stay at Paradise Palms today! 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.

Explore the charm of sunny Sarasota with a getaway to this coastal condo! Boasting 2 bedrooms, 1.5 baths, and a private balcony, this vacation rental is an ideal home base for exploring nearby beaches, unique attractions, and local eateries. When you aren't lounging by the community pool, head out to explore Siesta Key Village, sunbathe on the sands of Lido Key Beach, or cool off with an ice cream cone at Big Olaf Creamery! This condo is perfect for your next beach escape in the Sunshine State! -- THE PROPERTY -- Pool Access | Free WiFi | On-Site Laundry Sunshine, sand, and relaxation await at this Sarasota condo complete with a well-appointed interior and a location near beaches, dining hotspots, and local attractions like the Mote Marine Laboratory & Aquarium. Bedroom 1: King Bed | Bedroom 2: Queen Bed OUTDOOR LIVING: Private balcony, screened-in porch, community pool INDOOR LIVING: Flat-screen TV, leather sofa, beach decor KITCHEN: Fully equipped, dishwasher, drip coffee maker, microwave, refrigerator, stove/oven GENERAL: Air conditioning, suitable for children, suitable for elderly FAQ: Pet fee (paid pre-trip) PARKING: Community parking (2 vehicles), no covered parking -- THE LOCATION -- BEACHES + PARKS: Crescent Beach (3.3 miles), Siesta Key Beach (3.7 miles), Oscar Scherer State Park (8.2 miles), Lido Key Beach (10.2 miles), Venice Beach (14.6 miles), Manatee Public Beach (25.2 miles) THINGS TO DO: Siesta Key Village (3.3 miles), St Armands Circle Shops (9.1 miles), The John and Mable Ringling Museum of Art (10.1 miles), Mote Marine Laboratory & Aquarium (10.5 miles), DINING: Daiquiri Deck South Siesta Key (2.0 miles), Big Olaf Creamery (4.7 miles), Siesta Key Oyster Bar (4.7 miles), The Old Salty Dog Siesta Key (5.0 miles), AIRPORT: Sarasota-Bradenton International Airport (10.5 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 - Pet friendly w/ $50 fee (+ fees & taxes, 1 dog max) - 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 at check-in

Welcome to The Sarasota Starburst, a stylish mid-century sanctuary where 1960s Florida charm meets modern Florida luxury. Inspired by the iconic Sarasota School of Architecture movement, this home blends retro "pop" aesthetics with all the high-tech amenities a modern traveler needs. Whether you are here to lounge by the heated pool or need a bright, professional space for a "workation," this colorful retreat is your perfect Sarasota base. LOCATION HIGHLIGHTS - Central Sarasota: Nestled in a quiet neighborhood just minutes from the vibrant downtown scene. - Beach Proximity: A short drive to the world-famous white sands of Siesta Key and Lido Beach. - Neighborhood Vibe: Peaceful and residential, yet close to the best shopping and dining on the Gulf Coast. PROPERTY FEATURES - Heated Pool & Lanai: Enjoy year-round swimming in your private, screened-in oasis. - Pet-Friendly: A fully fenced-in backyard means your four-legged family members can vacation, too! - Work-from-Home Ready: A dedicated, professional workspace featuring a standing desk and dual monitors. - Retro Design: Authentic mid-century feel with "Sputnik" starburst wallpaper and curated pops of color. LIVING ROOM - Step into a sun-drenched, open-concept living area designed for relaxation. Large windows in the entry room flood the space with natural light, highlighting the clean lines and vintage-modern décor. - Whether you’re streaming your favorite shows on the Smart TV or curled up with a book, this room offers a bright and airy atmosphere for the whole group. - Sofa bed sleeps another 2 people KITCHEN AND DINING - The heart of the home is the "cozy-chic" kitchen, featuring sleek cabinetry and table seating for 4. - It is fully equipped with all the essentials for a home-cooked meal. Enjoy breakfast at the dining table, or head out to the covered patio to use the grill for a dinner by the pool. BEDROOMS AND BATHROOMS - Master Suite: Features a comfortable King bed, large closets, a Smart TV, and a private ensuite bathroom with a modern walk-in shower. - Second Bedroom: A beautifully decorated guest room with a Queen bed and plenty of natural light. - Bathrooms: Well-appointed with fresh linens and modern fixtures to ensure a spa-like stay. EXTRA PERKS - Beach Gear: We provide two beach chairs, a beach umbrella, and plush beach towels for your trips to the coast. - Laundry Room: Full-sized washer and dryer located in the laundry room for your convenience. - Parking: Attached garage suitable for a small vehicle, plus additional driveway parking. - Smart Tech: High-speed Wi-Fi and Smart TVs throughout - just bring your own streaming logins! NEARBY FAVORITES - The Ringling: Explore the historic circus tycoon’s estate and art museum. - St. Armands Circle: A premier destination for upscale outdoor shopping and gourmet dining. - Marie Selby Botanical Gardens: A world-class urban orchid garden on the bayfront. IMPORTANT INFO - Pet Policy: We are dog-friendly! Please let us know if you are bringing a pet. - Streaming Only: There is no cable TV; guests must use their own accounts for streaming services. - Pool Heat: The pool is heated for your comfort year-round (extra fee applies) - Quiet Hours: Please be mindful of our neighbors in this peaceful residential area. - There is a door camera for added security Experience the perfect blend of 1960s nostalgia and modern Sarasota living. From the "Starburst" kitchen to the sun-soaked lanai, every inch of this home is designed to help you relax, recharge, and enjoy the Florida sun. Book your stay at The Sarasota Starburst today! 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.

Harbor Towers Unit 330 by Tropical Sands Accommodations Harbor Towers Unit 330 is a comfortable two-bedroom, two-bath condo situated on the much coveted, serene and well landscaped pool side of the complex; with wonderful panoramic sunrises. This condo is located within the gated waterfront Harbor Towers community on Midnight Pass Road in Siesta Key. Designed for couples, friends, or small families, this inviting retreat offers a bright layout, coastal-inspired interiors, and a private screened lanai overlooking the pools and tropical community grounds. With easy access to Siesta Key Beach, dining, and island attractions, this condo is ideal for a relaxing extended stay. Highlights • Two-bedroom, two-bath condo • Queen bed, full bed, twin bed • Washer and dryer in unit • Screened lanai with seating • Gated waterfront Harbor Towers community with coded entry at all gates/doors • 13-night minimum stay community • Two heated pools and three Har-Tru tennis courts • BBQ grills and poolside patio, marina, fitness center, and sauna • Short distance to Siesta Key Beach and the Village Enjoy peaceful mornings and relaxing evenings on the screened lanai, where you can take in views of the pools and beautifully maintained tropical grounds and enjoy gentle coastal breezes. Guests of Harbor Towers enjoy a gated waterfront setting with resort-style amenities including two heated pools, three Har-Tru tennis courts, a marina, fitness center, and sauna, creating a comfortable and convenient island experience. The open concept living and dining area is designed for comfort and ease, featuring cozy seating, natural light, imported Italian porcelain flooring, and a layout that flows seamlessly to the screened lanai. This welcoming space is perfect for unwinding after a day at the beach or gathering together for meals and downtime. The kitchen is gorgeous and functional with premium cabinetry, counter space, a custom stone back splash, and stainless appliances, making it easy to prepare everything from simple breakfasts to relaxed dinners at home. The primary bedroom offers a relaxing retreat with a comfortable queen bed, ample storage with a walk-in closet, and a private ensuite bathroom. The second bedroom, located on the opposite side of the living and dining room for added privacy, features a full bed and a twin bed, providing flexible sleeping arrangements for additional guests and a reach-in closet. The hallway bathroom is conveniently located near the second bedroom and main living area, offering easy access for all guests. Each bathroom features granite and a custom vanity. Room Details • Primary Bedroom: Queen bed and ensuite bathroom • Second Bedroom: Full bed and twin bed • Second Bathroom: Hallway access Additional conveniences include an in-unit washer and dryer, elevator access within the building, and beautifully maintained community grounds throughout Harbor Towers. Your trip to the Beach is also covered as you have high and low beach chairs (6), umbrellas, some beach toys, beach towels 2 Igloo coolers. Tennis racquets/balls await your game on one of the three Har-tru clay courts on site. For those with sensitivities, the HVAC has been upgraded to include an “in duct” air purification system which actively reduces up to 99% of airborne contaminants; including allergens, bacteria, viruses, odors and VOC’s. This unit also has the rarely available Preferred and Assigned Carport Parking; close to the south building entrance. Your vehicle will stay cool and dry on the those hot days! Whether you are planning a seasonal escape or a longer Siesta Key getaway, Harbor Towers Unit 330 by Tropical Sands Accommodations offers comfort, location, and access to outstanding community amenities. Book your stay today and enjoy relaxed island living in one of Siesta Key’s most desirable waterfront communities.

WELCOME TO JAMAICA ROYALE VILLA Fully updated and recently renovated from top to bottom, this 1-bedroom villa is essentially brand new. With upgraded floors, stylish furniture, modern appliances, new lighting, and coastal finishes, it’s the perfect base for your Siesta Key beach vacation. Best of all, the complex features a private walkway leading straight to an exclusive stretch of world-famous white sand—an easy 4- to 5-minute stroll from your front door. PROPERTY HIGHLIGHTS Direct private walkway to the beach Three heated pools, including one near the Gulf Tennis courts, shuffleboard, and grilling areas in the complex Private patio with seating and dining table Fresh interiors with tile floors and modern coastal décor Uncovered parking located right at the villa entrance SLEEPING ARRANGEMENTS Bedroom: Two queen beds Living room: Queen sleeper sofa Sleeps up to 6 guests INSIDE THE VILLA Open living and dining area with new furnishings and Smart TV Fully equipped kitchen with stainless steel appliances, stone countertops, and cookware Updated bathroom with modern fixtures In-unit washer and dryer for convenience Keyless entry for easy check-in LOCATION Steps from pools and a short 4-5 minute walk to the sand via private beach access 1.5 miles to Siesta Key Village for shopping, dining, and live music Local ride services available so you can park once and explore hassle-free GOOD TO KNOW Single-story villa in the garden section of the complex Garden and courtyard views from the living room and lanai Photos reflect the current renovation BOOK YOUR STAY AT JAMAICA ROYALE VILLA TODAY Enjoy modern comfort, three heated pools, private beach access, and an unbeatable Siesta Key location for your next getaway. Next door complex is under construction. Unfortunately, we don’t have any say in the matter. Xplorie Activities and Airport Transportation -One complimentary activity per day: bike rental, kayak rental, dolphin cruise tour, or Ringling Museum admission -Limited to one person per day; additional guests can join for a fee -Round-trip airport transportation included for up to 3 passengers from SRQ or TPA with advance reservation (driver tip appreciated) -Activities subject to availability and change; non-cumulative and non-transferable -Not available for stays of 25 nights or longer IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Harbor Towers Unit 721 by Tropical Sands Accommodations Harbor Towers Unit 721 is a recently refreshed two-bedroom, two-bath condo located within the gated waterfront Harbor Towers community on Midnight Pass Road in Siesta Key. Positioned on a higher floor, this inviting retreat offers a bright, open layout with a private screened lanai and convenient access to Siesta Key Beach, dining, and island attractions. Ideal for couples, friends, or small families, this condo is well suited for a comfortable extended stay on the island. Highlights • Two-bedroom, two-bath condo • King bed, two twin beds • 13-night minimum stay community • Washer and dryer in unit • Screened lanai with seating • Recently refreshed interior • Gated waterfront Harbor Towers community • Two heated pools and three Har-Tru tennis courts • Marina, fitness center, and sauna • Short distance to Siesta Key Beach and the Village Relax on the screened lanai, where you can enjoy elevated views and gentle coastal breezes throughout the day. As a guest of the Harbor Towers community, you will enjoy access to a gated waterfront setting featuring two heated pools, three Har-Tru tennis courts, a marina, fitness center, and sauna, creating a resort style atmosphere for your stay. The open concept living and dining area is filled with natural light and designed for comfort, offering plush seating and a welcoming layout that makes it easy to unwind after a day at the beach. Sliding doors connect the living space to the screened lanai, extending the living area outdoors. The kitchen is well equipped with granite countertops, ample cabinetry, and essential appliances, making meal preparation simple whether you are enjoying quick breakfasts or relaxed dinners at home. The primary bedroom serves as a peaceful retreat with a comfortable king bed, generous storage, and a private ensuite bathroom featuring a walk-in shower. The second bedroom offers two twin beds and is conveniently located near the hallway bathroom, which also features a walk-in shower. Room Details • Primary Bedroom: King bed and ensuite bathroom with walk-in shower • Second Bedroom: Two twin beds • Second Bathroom: Hallway access with walk-in shower Additional conveniences include an in-unit washer and dryer, elevator access within the building, and beautifully maintained community grounds throughout Harbor Towers. Whether you are planning a seasonal escape or an extended stay on Siesta Key, Harbor Towers Unit 721 by Tropical Sands Accommodations offers comfort, location, and access to exceptional community amenities. Book your stay today and enjoy relaxed island living in one of Siesta Key’s most desirable waterfront communities.