Summerland Key, FL Vacation Rentals

Newly renovated & expanded, amazing pool, dockage & boating access on Summerland Key Luxury Waterfront Living on Summerland Key Escape to the Florida Keys and indulge in island living at its finest in this spacious 5-bedroom, 3.5-bath pool home on coveted Caribbean Drive East. Designed for both relaxation and adventure, this gated retreat offers direct deep-water boating, open water views and breathtaking sunset hues. A gorgeous remodel brings modern elegance throughout. The new primary suite is a private sanctuary with a king bed, a spa-inspired en-suite bath featuring a huge walk-in shower, dual vanities, and a soaking tub — plus a private waterfront patio perfect for morning coffee or evening cocktails. Additional guest accommodations include two queen bedrooms on the main level that share an upgraded Jack-and-Jill bathroom, plus thoughtfully designed spaces that balance comfort and style. Gather in the brand-new, top-of-the-line kitchen, enjoy meals in the light-filled dining area with canal views, or relax in the living spaces that open seamlessly to the outdoors. The large screened porch is ideal for al fresco dining, while the open pool deck invites sun-soaked afternoons beside the deep, heated pool. With plenty of dockage, boating enthusiasts will love the easy access to world-class fishing and snorkeling. Ample parking ensures convenience for you and your guests. Home features: - Renovated kitchen with new cabinets, appliances and fixtures - New king primary suite with luxurious ensuite - 4 queen bedrooms with 2 full baths - Canal-view living and dining areas - Large screened porch and multiple waterfront patios - Main-level laundry and half bath - Pool, heat optional in winter - 80 feet of deep-water dockage and a kayak/paddle board ramp Rental Information: This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Primary renter must be 25 years or older. Overnight occupancy is limited to 10 guests, and all guests must be registered with the property manager. No smoking. Well-behaved dogs are considered with manager approval and a $250 nonrefundable fee. Pool heating is available for an additional $500 per month. Discover your private slice of paradise on Summerland Key, where luxury, comfort and the Florida Keys lifestyle come together. Guests have the house to themselves. A car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.

🏡 Amenities: Dock, Guest Cottage, Pool, Spa, Outdoor Kitchen, Firepit 🌊 Kayaks, and Paddle Boards 📍 30 Minutes to Key West and Marathon 🐶 Dog Friendly 🤝 24/7 Guest Support Welcome to Sirena Key, a luxury oceanfront gated estate in the exclusive island community of Summerland Key in the Florida Keys. This private vacation rental is designed for families and groups seeking the perfect blend of resort-style amenities and the comforts of home. Step through the gates and you’re greeted by a charming garden with bistro seating, a tranquil spot to relax while children enjoy the open grassy lawn. The estate includes a spacious main house with 4 bedrooms and 3.5 bathrooms, as well as a private guest cottage with a living room, pullout sofa, full kitchen, dining area, bed and bathroom. Together they create the ideal setup for multi-family getaways, offering both elegant gathering spaces and private areas. Outdoors, unwind beside the sparkling pool and spa, complete with hotel-style loungers, a cabana bed, hammock, and umbrellas. A full outdoor kitchen with seating makes alfresco dining effortless, while kayaks and paddleboards invite adventure on the water. Evenings can be spent gathered around the firepit or at the private oceanfront lounge, perched at the edge of the ocean with shaded loungers and breathtaking views. With space for up to 14 guests, Sirena Key offers the ultimate Florida Keys experience, just 30 minutes from both Key West and Marathon. 🍽️ INDOOR MODERN KITCHEN + DINING -Chef’s kitchen with induction cooktop, stainless steel appliances, and beverage fridge -Counter seating for 3, and formal dining table for 6 -Open-concept living room with large sectional, Smart TV, and motorized blackout blinds ✨ ENTERTAINMENT + LOUNGING SPACES -Movie theater with projector, oversized sectional, motorized blackout blinds, and pool + ocean views. -Game room with pool table, shuffleboard, Smart TV, motorized blinds, and direct patio access with chic outdoor dining table. -Secret garden entry with lounge seating and dining table. 🛏️ MAIN HOUSE BEDROOMS All bedrooms feature the following amenities: ✔ Premium beds, pillows, linens, and sheets ✔ Ceiling fans ✔ Tv’s ♛ Primary Suite (2nd Floor): King bed, spa-style ensuite, walk-in closet, desk, seating area, Smart TV, water views, coffee nook, motorized blackout blinds. Ensuite includes double vanity, spa tub, dual shower-heads, and private toilet room. -First-Floor Bunk Room: Four twin bunks, sectional, Smart TV, blackout blinds, private porch with dining table for 4, ensuite bathroom with shower and vanity. -First-Floor Queen Bedroom #1: Queen bed, Smart TV, access to Jack-and-Jill bathroom with shower and vanity. -First-Floor Queen Bedroom #2: Queen bed, desk, Smart TV, Jack-and-Jill bathroom access. 🏡 PRIVATE GUEST COTTAGE The separate guest cottage is a fully equipped retreat of its own, perfect for families traveling together or guests who want more privacy. -Studio layout; Queen bed -Living room with pull-out sofa -Kitchen + dining area -Private bathroom with shower and vanity 🛁 BATHROOMS All full bathrooms are generously stocked with: ✔ Shampoo & conditioner ✔ Body soap ✔ Fluffy towels ✔ Toilet tissue -Primary Ensuite: Spa tub, dual shower heads, double vanity, motorized blackout blinds, private toilet room -Bunk Room Ensuite: Shower and vanity -Jack-and-Jill Bath: Shared by two queen rooms, shower and vanity -Half Bath: Vanity, sink, toilet, washer/dryer and storage -Cottage Bathroom: Shower and vanity 🌴RESORT-STYLE OUTDOOR SPACES Sirena Key’s outdoor spaces are designed like a private resort. -Automatic front gate for secure entry, expansive driveway with space for multiple vehicles. -Pool and spa with cabana-style bed, hotel-style loungers, umbrellas, and hammock -Pergola with large sectional lounge sofa -Full outdoor kitchen with seating, Lynx propane grill, Asado grill, and prep space -Kayaks and paddleboards available for guest use -Garden patio and shaded dining areas 🌊 OCEANFRONT EXPERIENCES This home takes oceanfront living to the next level! -Private dock with fish-cleaning station, running water, and hose -Bait fridge -Separate oceanfront lounge right with firepit, chairs, and 3 loungers featuring built-in personal shade canopies -Boat lifts are for owner use only and not available to guests ⚠️ OCEANFRONT SAFETY NOTE Sirena Key is situated directly on the ocean with a private dock and open water access. Due to the home’s oceanfront setting and pool design, extra care and supervision are required when children are present. Children must be fully supervised at all times when outdoors or near the pool, dock, or water. Parents or guardians are responsible for ensuring the safety of all members of their party during their stay. This home is best suited for guests who are comfortable managing an oceanfront environment. 📍POINTS OF INTEREST + LOCATION HIGHLIGHTS Sirena Key is located in Summerland Key, one of the most desirable islands in the Florida Keys, just 30 minutes from Key West & Marathon. Guests enjoy easy access to marinas, fishing, snorkeling, and world-class attractions. -Big Pine Key & National Key Deer Refuge – 15 minutes -Bahia Honda State Park – 25 minutes -Marathon – 35 minutes -Key West – 30 minutes -Islamorada – 1 hour 15 minutes -Key Largo – 2 hours EXTRA DETAILS -High-speed WiFi throughout the property -Motorized blackout blinds in primary bedroom, primary bathroom, game room, living room, bunk room, and theater -Washer and dryer -EV charger available (requires an adapter for Teslas) -Responsive 24/7 guest support team Book your stay at Sirena Key and enjoy the ultimate Summerland Key vacation rental. A private Florida Keys estate with luxury amenities, a separate guest cottage, and unforgettable waterfront living. ⚠️Other Things to Note: -Guests are welcome to use the boat dock during their stay. It can accommodate boats up to 40 ft in length. Please note that boats with more than a 3 ft draft may not be suitable. -Boat lifts are for owner use only and not available to guests HOUSE RULES: Check-in time: 4:00 PM Check-out time: 10:00 AM All guests must sign our rental agreement as mandated by Florida Law. -We require the exact number of people, full names, and ages of who will be in the home. -The minimum rental age is 25. A picture ID must be provided to the company no less than 72 hours (about 3 days) before arrival. -If you would like the pool heated during your stay, there is a $40 fee per day or $1,000 per month. Please coordinate with us prior to your arrival so that we can arrange for the heater to be on. -Please provide an accurate guest count. -No smoking or vaping. If evidence is discovered of either smoking or vaping, the guest will be subject to a fine of up to $1,000 -No parties or events. If unauthorized persons are discovered on the premises, guests will be subject to additional fees and/or immediate eviction. -Quiet time is from 10:00 PM - 8:00 AM -This property is equipped with security cameras on the outside of the property at the entrance and pointing at the dock. These cameras are used during the check-in process to verify identity and guest count. If there is an incident, we will review the footage. There are no cameras inside the property or pointing toward the pool area. Starter Supplies: We provide trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate this home’s maximum occupancy for the first three days of your stay. Same-Day Bookings: Same-day bookings require approval from the company. We will ask you to provide information on your group and the purpose of your stay. If your stay is approved, we require a government-issued ID for identity verification. Your phone number must match the phone number on your account, or we will not be able to honor your reservation. Same-day reservations will not be accepted after 2:00 PM. All same-day reservations require at least 3 hours before check-in. We may have to extend check-in time to later than 4:00 PM. Pet Policy: This property is dog-friendly, with an additional $750 per month, per pet. For stays of two months or longer, the fee is $2,000 per month, per pet. While staying with us, you are responsible for the actions of your pet. Please keep your dog(s) off the furniture and pick up all waste. All waste should be bagged and disposed of in the outside trash bin. Failure to comply with our pet policy may result in an additional $100 fee. Please let us know if you will be bringing your dog (only dogs under 25 lbs are permitted, sorry). Baby Bundle: If you have little ones, we offer: Pack-n-play with a thicker mattress & a high chair for $65 per stay. Please make your request at the time of booking or 24 hrs prior to your arrival. Property Care Instructions: Treat this home like your own. -Any/all outdoor umbrella(s) must be placed in the closed position when not in use and at the time of check-out. This must be done in order to prevent breakage due to weather conditions. Failure to comply may result in an additional charge. -Please ensure that the grill is covered when not in use. This helps to maintain the grill’s condition for future guests. Failure to comply may result in a cleaning or maintenance fee. Mid-Stay Cleaning Requirement: For all extended stays of 30 nights or longer, a mandatory mid-stay cleaning is required every 30 days. If your reservation is 60 days, two mid-stay cleanings will be required, and so on. This helps keep the home maintained during longer stays and ensures everything stays in great condition. Mid-Stay Cleaning Fee: $750 (Main House + Cottage) We’ll reach out after booking to schedule the mid-stay cleaning(s) and send the payment link.

Settle into island life at Sailfish Retreat, a 3-bedroom, 2-bathroom canalfront home on Cudjoe Key. Enjoy a private pool, covered outdoor living and concrete dockage for a boat up to 25 feet. With quick boating access to Cudjoe Bay, the reef and backcountry, it’s an ideal monthly escape for boaters, anglers and families. Welcome to Sailfish Retreat, your waterfront escape on Cudjoe Key! This like-new 3-bedroom, 2-bathroom monthly rental sits on a boating canal with a short run to open water. A private pool (photos to come) between the house and canal creates an inviting place to cool off, relax and enjoy the tropical waterfront setting. Comfortable Island Living Inside, the spacious living area features a large leather reclining sectional with plenty of room to unwind. The well-stocked kitchen and dining area offer seating for four at the table and four at the breakfast bar, making meals at home easy and comfortable. Sleeping Arrangements - The primary bedroom has a king bed, walk-in closet and en-suite bathroom with a soaking tub and separate shower. - The second bedroom has a queen bed and access to the shared hallway bathroom. - The third bedroom has two twin beds and access to the shared hallway bathroom. Pool and Outdoor Living Step onto the covered porch to enjoy views of the pool and canal. Take a refreshing swim, relax poolside or cook your catch on the gas grill and dine outdoors in the shade. Please be aware that the private pool is not heated. Stay Connected High-speed internet and WiFi make it easy to stay connected. Bring your own streaming services to enjoy on the flat-screen smart TVs in the living area and each bedroom. Bring Your Boat A ride down the canal from the concrete dock takes you to Cudjoe Bay, with approximately a 20-minute run to the reef. Bow and Kemp channels also provide access to the backcountry for fishing and exploring. There is room for a boat up to 25 feet at the dock. The boat lift, which is not pictured, and downstairs storage are reserved for owner use only. Explore Cudjoe Key Cudjoe Key is a laid-back island approximately 22 miles from downtown Key West. Some of the Lower Keys’ most popular restaurants are nearby, including Square Grouper and the island steakhouse Broil. Public and private boat ramps are available in the area, and a large grocery store is just a few miles away. Whether your ideal Keys stay includes fishing, boating, relaxing beside the pool or simply enjoying the waterfront, Sailfish Retreat offers a comfortable home base for a month or longer in the Lower Keys. Good to Know - This home requires a minimum 28-day stay per Monroe County ordinance. - The primary guest must sign a rental agreement regardless of booking platform. - Proper county and state taxes are collected regardless of booking platform. - The primary renter must be 25 or older. - Overnight occupancy is limited to a maximum of six people. All overnight guests must be registered with the property manager. - One small to medium dog is permitted with manager approval and a $250 nonrefundable pet fee. - Electric usage is capped at $300 and water/sewer usage is capped at $200. Any overages will be billed to the guest. - The private pool is not heated. - No smoking is permitted.

Gorgeous canalfront pool home close to open water on Cudjoe Key Escape to a slice of paradise on Cudjoe Key, where luxury meets tranquility in this stunning 3-bedroom, 2-bathroom stilted home with pool on a boating canal. This monthly rental offers a perfect blend of upscale comfort and coastal charm, providing an idyllic retreat for your Key West getaway. Step inside to discover a beautifully appointed interior, where every detail exudes warmth and sophistication. The spacious living area invites you to unwind with plush furnishings and stylish accents, while large windows bathe the space in natural light and offer enchanting views of the surrounding waterfront paradise. Prepare delicious meals in the gourmet kitchen, equipped with modern appliances, sleek countertops, and ample cabinet space. Adjacent to the kitchen, the dining area sets the stage for memorable gatherings with loved ones, while sliding glass doors seamlessly connect the indoor and outdoor living spaces. Venture outside to experience the ultimate in outdoor living, where a waterfront pool beckons you to soak up the Florida sunshine and cool off with a refreshing swim. Lounge on the expansive pool deck, furnished with comfortable seating and dining areas, as you savor the gentle sea breeze. For a truly unforgettable experience, ascend to the rooftop deck and witness the spectacle of the sun rising and setting over the horizon, casting a mesmerizing palette of colors across the sky. Boating enthusiasts will delight in the convenience of the 40 feet of dock space, just steps from your door. Launch your own vessel or explore the surrounding waters by kayak or paddleboard, immersing yourself in the natural beauty and serenity of the Florida Keys. Whether you’re seeking adventure on the water or simply seeking solace amidst the beauty of the outdoors, this exquisite vacation rental offers the perfect blend of luxury, comfort, and coastal living for your Florida Keys escape. Indulge in the ultimate vacation experience at this stunning waterfront oasis on Cudjoe Key. Please note that during your stay, the owner’s boat will be stored on the lift and his vehicle will be parked under the house, but there’s still plenty of room for you to park your vehicles and trailer. The primary guest must sign a rental agreement. This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 6 people, and all guests need to be registered with the property manager. No smoking. Small dog permitted with manager approval and nonrefundable fee. There’s a cap on electric ($300) and water/sewer ($150). Pool heat is an additional $15 per day. Guests have the house to themselves. A car is recommended. A car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.

Oceanside monthly rental in the Lower Florida Keys with 60 feet of concrete dockage, bait freezer, fish-cleaning station, and quick open-water access — ideal for anglers, boaters, and extended Keys stays. Welcome to Bahama Breeze in the Keys, a relaxed oceanside retreat designed for extended stays in the heart of Cudjoe Key. Tucked into a quiet residential neighborhood, this waterfront home blends island comfort with excellent boating access and easygoing coastal living. Inside, the open and airy layout features warm pine floors, vaulted ceilings, and two distinct living areas — perfect for spreading out, entertaining, or unwinding after a day on the water. The updated kitchen is equipped with stainless-steel appliances and quartz countertops, making everything from casual breakfasts to sunset dinners effortless. The main level offers two king bedrooms, comfortably furnished for restful nights, along with a shared full bathroom. A spiral staircase leads to a cozy open loft with a full-size bed, ideal for additional guests. The great room also includes a comfortable fold-out sofa, plus a convenient half bath off the living area. Outdoor living is where Bahama Breeze in the Keys truly shines. A wrap-around covered porch, accessible from every room, invites you to enjoy cooling sea breezes throughout the winter months. Boaters and anglers will appreciate: - 60 feet of concrete dockage - Swim ladder - Fish-cleaning station - Bait freezer and ice maker - Lots of outdoor seating - Outdoor shower with hot and cold water - Gas grill - Fully fenced yard Whether you’re heading out at sunrise or winding down dockside in the evening, everything is in place for effortless Keys living. Comforts & Amenities: - High-speed internet - Smart TVs in the living room, both bedrooms and the loft - Lockable storage shed for personal items or outdoor gear - Contact-free check-in and check-out Important Notes & Rental Details: - Minimum 28-day stay required by Monroe County ordinance - Primary guest must sign a rental agreement, regardless of booking platform - Proper county and state taxes collected, regardless of booking platform - Primary renter must be 25+ years old - Maximum overnight occupancy: 6 guests - No smoking on the property - One small or medium dog permitted with manager approval and a $250 nonrefundable fee. No cats. - The downstairs storage, davits and kayaks are not available for renter use. - Utilities included with caps on usage of $300 for electric and $150 for water Bahama Breeze in the Keys is ideal for guests seeking a true long-term oceanside Keys experience — where boating days, porch evenings and unhurried island living come together effortlessly. Guests have exclusive use of the entire home. A car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have ride-share services and limited taxi service.

Pet-friendly 3 bed/2 bath boating home on Cudjoe Key Canalfront 3 bedroom/2 bathroom home with excellent oceanside boating access. Open floor plan with a large kitchen, stainless appliances, plank flooring, beautiful tray ceiling over the living area and large windows. French doors out to the covered porch with seating overlooking the canal. Super-comfortable reclining sectional with 55-inch TV in the living room. Satellite TV and high-speed Internet and WiFi. Master suite has a king bed, walk-in closet, double sinks and a shower. Second bedroom (king bed) and third bedroom (queen bed) share the hall bathroom with a shower/tub combo. 30-foot concrete dock. Concrete pad underneath the house. Plenty of off-street parking for your vehicles and trailer. No outside storage. Please note: This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Primary renter must be 25 or older. Overnight occupancy is limited to 6 people, and all overnight guests need to be registered with the property manager. No smoking. One pet permitted with manager approval and nonrefundable $250 pet fee. There’s a cap on electric ($250) and water/sewer ($150). Guests have the house to themselves. A car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.

Spectacular Sunsets & Bay View | Waterfront Lounge Area | 2 Kayaks Planning a long-term stay in the Florida Keys? Book this 2-bedroom, 2-bath Cudjoe Key vacation rental! Enjoy slow mornings with coffee on the spacious deck, then take the provided kayaks out for a spin or beachcomb at Bahia Honda State Park. Later, gather around the fire pit and savor the sunset. No matter who you’re traveling with, this home offers the perfect base for a memorable month in the Sunshine State! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Living Room: 1 queen sleeper sofa - Additional Sleeping: 1 queen air mattress OUTDOOR LIVING - Bay & sunset views - Deck w/ seating & Smart TV - Gravel patio, wood-burning fire pit, gas grill - 2 kayaks - Private dock, canal access INDOOR LIVING - 3 Smart TVs - Dining table, dry bar KITCHEN - Refrigerator, stove/oven, dishwasher - Dishware/flatware, children’s dinnerware, cooking basics - Keurig coffee maker (starter pods provided) - Blender, ice maker - Microwave, toaster, toaster oven GENERAL - Free WiFi - Central A/C, ceiling fans - Central/electric heating - Linens/towels, iron/board - Washer/dryer (detergent provided) - Trash bags, paper towels - Hair dryer, complimentary toiletries FAQ - Pet fee (paid pre-trip) - 4 exterior security cameras (facing out) ACCESSIBILITY - Single-story home, exterior stairs required PARKING - Carport (2 vehicles) - Gravel driveway (2 vehicles) -- THE LOCATION -- - Walk to grocery store, coffee shop & restaurant - Near kayaking areas, boat rentals & fishing charters - 11 miles to Sugarloaf Beach & 14 miles to Bahia Honda State Park - 19 miles to Key West Tropical Forest & Botanical Garden - 22 miles to Key West: Smathers Beach, parks, shops, galleries, cafes, bars, restaurants - 21 miles to Key West International Airport & 138 miles to Miami International Airport -- REST EASY WITH US -- Property Manager 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 or vaping of any kind, including marijuana - Pet friendly w/ $90 fee (+ fees & taxes; dogs only, 1 max) - 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 ADDITIONAL INFORMATION - This property sleeps 4 guests in 2 beds, with room for 6 total by using the queen air mattress - This single-story home requires exterior stairs to enter - Your safety matters. This property features 4 exterior security cameras: 1 camera is on the side facing the homeowner’s boat, 1 camera is in the carport facing the front yard and street, 1 camera is at the top of the entry stairs facing the staircase and side yard, and 1 camera is on the back facing the backyard and dock area. These cameras are outward facing and do not look into any interior spaces. They record sound and video when activated by motion

Villa Jekjak- 4 BDR, luxury residence with pool & beach Enjoy the unobstructed 270-degree ocean view in this newly renovated beachfront residence. Located in the most exclusive part of Cudjoe Gardens this 2- story house is surrounded by the water on 3 sides. Three bedrooms and two bathrooms are impressively decorated in a soft coastal palette and are located on the second main living floor. Amble of natural light emphasizes the open and easy-flowing design of the main floor. Well-equipped chefs kitchen has top-of-the-line appliances and is a perfect retreat for culinary-inspired guests. Highlighted by the walls of glass doors, Family Friendly floorplan combines the living room, dining room and opens to the oceanfront terrace.  The vaulted ceiling adds great drama to the space. Light & Airy Master Suite features King Bed, a private Master Bathroom with a stand-up shower, and a large walk-in closet. The guest wing offers generously scaled 2 bedrooms and a shared bathroom. The downstairs Guest Quarter enclosure has an additional private queen bedroom, rec room, TV area, and a wet bar and full bathroom. The private pool is nestled on a sandy beach and surrounded by meticulously maintained grounds. Deep access to world class fishing and free dockage makes this house a boaters paradise! This house is truly Paradise Found! The property is PET-friendly with a non-refundable PET fee. Additional features: Washer & Dryer Central AC & ceiling fans throughout Starter supply paper products Starter set cleaning products Linens, bath, and pool towels Kitchen cookware, dishes, flatware, glassware Wireless high-speed internet Fully fenced private residence Housekeeping services available Original Art Private dock Private Beach and a hammock Outdoor Shower BEDROOMS>>Master- King Bed Guest Bedroom #1- Queen Bed Kids Room- Bunk Bed Downstairs Guest Quarter- 1 Queen Bed

Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you’re relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more! Welcome to your perfect getaway! This charming home features a spacious open-concept floor plan designed for relaxation and connection. The main living space includes two twin sleeper sofas, while the bedroom features a queen bed - making it ideal for families or groups of friends. Natural light pours into the airy interior, complementing the seamless flow between the living, dining, and kitchen areas. Whether you’re enjoying quiet moments or gathering for meals, this inviting space offers the comfort and convenience you need for a memorable stay. Bedroom 1: Queen Bed Extra sleeping: two twin sofa beds in living room Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. How to access: Stair access only Parking Information: Private parking is available in front of the home. This home is conveniently located, offering easy access to everything Sugarloaf Key and the surrounding Keys have to offer but still maintaining peacefulness surrounded in nature. A car is recommended for exploring the area, with ample parking available at the property. Enjoy a short drive to nearby beaches, marinas, and local attractions. Key West, with its vibrant nightlife, unique shops, and historic sites, is just a 25-minute drive away. For those looking to explore by bike or foot, the scenic Overseas Highway provides stunning views and plenty of spots to stop and take in the beauty of the Keys. Private Washer/Dryer: Conveniently located in the home. Parking Information: Private parking is available in front of the home. Pet-Friendly Home: Dogs under 25 lbs are welcome! $15 per night, per pet, Maximum of 2 pets This property is a 3-night minimum stay.

Gorgeous pool, big dock & easy ocean access from this 5 bed/4 bath home on Big Pine Key Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offers unparalleled luxury and convenience, just seconds away from Pine Channel on the oceanside of Big Pine Key. Nestled just four houses in from Pine Channel, this stunning property features a breathtaking custom pool and spa, perfect for unwinding after a day of exploring the pristine waters. With a 60-foot concrete dock equipped with large piles with fenders, accommodating your big boat has never been easier. Convenient steps lead down into the deep water 70-foot wide canal, providing effortless access for swimming, kayaking, or paddleboarding. And keep your eyes peeled for endangered manatees, frequent visitors to the clear, deep canal. Boasting 2,400 square feet of meticulously designed living space, this isn’t your average Keys rental! The main floor features a king en suite with walk-in closet and a second king bedroom, plus a full bath off the hall. Upstairs, discover three additional bedrooms, including a king en suite with sleeper sofa, desk, large TV with game console and balcony with panoramic open water views. With two queen beds in the 2nd upstairs bedroom, another queen bed in the third and a full bath and seating area off the hall, there’s ample space for everyone to relax in comfort. Indulge your culinary aspirations in the fully equipped kitchen, complete with modern appliances including an instant pot, sous vide, and KitchenAid stand-alone mixer. Enjoy meals at the breakfast bar for three or gather around the dining room table that comfortably seats six. For outdoor dining, head to the poolside area. Unwind on one of the two covered porches, each offering peekaboo views of the open water. The waterfront custom pool and spa, featuring a waterfall and tanning ledge, provide the ultimate relaxation spot. Completed in March 2023, the pool measures 14 by 30 feet and boasts a stunning finish with pebble tech and custom tile. The spa backs up to a custom bar with a quartzite countertop, offering the perfect vantage point for soaking in the views of the pool and canal. There’s lockable storage downstairs for all of your gear, plus parking for three vehicles and a boat trailer. Experience luxury living on Big Pine Key – book your stay at this spectacular vacation rental today! The primary guest must sign a rental agreement. This is a minimum 28-day rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 12 people, and all overnight guests need to be registered with the property manager. Well-behaved dog permitted with manager’s approval and payment of nonrefundable $250 fee. No smoking. There’s a cap on electricity ($300) and water/sewer ($200). Pool heat available upon request for an additional charge.

Welcome to Fishermen’s Paradise, a beautifully appointed open-water retreat on Big Pine Key. Enjoy a private heated pool, 220 feet of dockage for one guest boat, outstanding access to the backcountry, Gulf and Atlantic, and frequent visits from the island’s famous Key Deer. This Lower Keys escape is designed for unforgettable days on and off the water. Welcome to your perfect island retreat on Big Pine Key. Freshly remodeled and thoughtfully designed, this three-bedroom, four-bath waterfront home combines modern comfort with the natural beauty of the Lower Florida Keys. With 2,000 square feet of elevated living space, a private resort-style pool, private dockage for one guest boat and sweeping open-water views, this is the ideal place to relax, explore and enjoy life on the water. Boaters and anglers will appreciate the exceptional waterfront setup. Guests are welcome to dock one boat at the property during their stay, in accordance with Monroe County regulations. The 220-foot dock offers some of the best boating access in the Lower Keys, with approximately 5 feet of water depth at the end of the dock. Amenities include a step-down platform, swim ladder, power, water and an outdoor shower for rinsing off after a day on the water. From here, you’ll enjoy quick access to the backcountry flats, Gulf waters and the Atlantic, making it easy to spend your days fishing, diving, snorkeling or exploring the countless islands and sandbars that make the Lower Keys so special. Anglers will appreciate the dedicated bait freezer located in the downstairs storage, along with a selection of fishing rods available for guest use. After a day on the water, enjoy a game of cornhole while taking in the waterfront setting. Want to explore beyond the boat? A local outfitter can deliver bikes, kayaks and paddleboards directly to the property. Your property manager can also provide recommendations for fishing charters, boat rentals and other local adventures. Inside, you’ll find a beautifully updated kitchen equipped for everything from quick breakfasts to fresh-catch dinners. A wine cooler and small ice maker make entertaining easy. To make your arrival even more relaxing, guests may arrange grocery delivery through their preferred delivery service before check-in, and we’ll gladly place everything inside the home so your vacation can begin the moment you walk through the door. Each bedroom serves as a private retreat with its own en-suite bathroom, generous storage space and smart TV with DirecTV Stream. Outside, unwind by the resort-style pool and take in the open-water views. The pool is heated from mid-October through mid-April, making it comfortable to enjoy during the cooler months. A selection of pool toys adds to the fun for guests of all ages. Keep an eye out for the island’s famous Key Deer, which are frequently spotted passing through the property. Found only in the Lower Florida Keys, these endangered miniature deer provide a unique wildlife-viewing opportunity that many guests remember long after their stay. **Sleeping Accommodations** • Primary Suite: King bed and large tub/shower combination • Guest Suite 1: Queen bed plus oversized twin chair/sleeper and tub/shower combination • Guest Suite 2: Queen bed with private shower • Living Room: Queen sleeper sofa Big Pine Key is home to the National Key Deer Refuge, miles of scenic bike paths, excellent kayaking trails and some of the most pristine natural landscapes in the Florida Keys. Conveniently located near local restaurants, shops and marinas, the home is just 20 miles from Marathon, 31 miles from Key West and only 5 miles from Bahia Honda State Park, widely regarded as one of the most beautiful beaches in the Florida Keys. Spend your days boating, fishing, snorkeling, kayaking, wildlife watching or simply relaxing poolside with water views. Whether you’re planning a fishing trip, a family getaway or a relaxing escape by the water, this exceptional waterfront home offers the perfect setting for an unforgettable Keys vacation. **Good to Know** • Primary renter must be at least 25 years old and sign a rental agreement. • Maximum overnight occupancy is 8 guests. • All guests must be registered with the property manager. • No smoking or pets permitted. • Guests may bring and dock one boat and trailer during their stay, in accordance with Monroe County regulations. • The home is fully licensed for short-term vacation rentals, and all required county and state taxes are collected regardless of booking platform. • Shorter stays may be available when calendar openings permit.

Loggerhead Lagoon is a stunning, tropically themed, 3-bed 2-bath home located on a large private lot that offers covered parking, a boat dock, and direct access to the Gulf of Mexico. This rare find boasts a lush outdoor area, full of beautiful palms, sun loungers, and tons of FL sunshine! Located in Sugarloaf Key, 19 miles from Key West and world famous Duval Street. Looking to unwind? You won’t find a better option for your month-long (or more) stay in paradise Spread out and spend quality family time in the open floor plan interior. Highlights of this modern home include tall vaulted ceilings, high-end finishings, tile floors, impact windows, sliding glass doors & a walk-in laundry room. Cook homemade meals in the kitchen with stainless steel appliances and custom cabinetry to maximize space. Bedroom 1 - Primary king with en-suite bathroom Bedroom 2 - Queen bed, filled with natural light & closet space Bedroom 3 - Queen size bed, spacious, closet space Extra Sleeping - Queen sleeper sofa for extra guests joining! Relax on the roomy porch perfect for entertaining guests and late night stargazing. Perfect for anyone looking for a month-long getaway that wants to enjoy the true benefits of staying in a waterfront island retreat in the Lower Keys! Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. How to access: Stair access only Travel by water or foot at this waterfront property! Boat docking available in the back of the home along with private vehicle parking. - Private washer/dryer in home. - Parking Information: Off-street covered parking for 2 vehicles. - This home is pet friendly! Dogs must be 40lb or under. $250 per stay. - All advertising should reflect a 28-day minimum stay requirement and monthly rates for rental or lease. All rentals should be for 28+ consecutive days and to the same tenant. It is unlawful for any landlord, tenant, agent, or other representatives to rent, lease, advertise or offer for rent any dwelling unit for vacation rental use in any district where vacation rental use (less than 28 days) is prohibited.

Amazing 3 bed/3 bath waterfront retreat with pool & dockage on Big Pine Key Indulge in the ultimate escape at this secluded monthly vacation rental on Big Pine Key. Nestled in serenity, this hidden gem sits on the open water close to Bogie Channel and offers a tranquil retreat away from the hustle and bustle. Immerse yourself in luxury with a private pool, perfect for refreshing dips on warm days. Situated on a large lot, this property boasts 100 feet of dockage, providing ample space for water enthusiasts to dock their boats and embark on aquatic adventures. The primary suite is a haven of comfort, featuring a king bed, an en-suite bathroom and a day bed with trundle. The 2nd and 3rd bedrooms are equally inviting and outfitted with two queen beds each to ensure a restful night’s sleep for all. The living area is generously spacious, providing a comfortable setting for socializing and relaxation. Step outside to the covered porch, where you can unwind amidst the beauty of the natural surroundings. This vacation rental seamlessly combines convenience and luxury for a truly rejuvenating stay. Escape to the tranquility of Big Pine Key and experience the epitome of relaxation at this secluded oasis, complete with a pool, open water views, and all the amenities needed for an unforgettable vacation. Big Pine Key strikes a perfect balance between nature and convenience, with stores and restaurants surrounded by miles of biking and walking trails, tropical hardwood, and pine forests. The island’s National Key Deer Refuge, home to 20 endangered species, including the iconic Key Deer, enhances the natural beauty of this open water retreat. The primary guest must sign a rental agreement. This is a 28-day minimum rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 8 people, and all guests need to be registered with the property manager. Absolutely no smoking or pets. There’s a cap on electric ($300) and water/sewer ($200). Pool heat is available upon request at an additional cost of $400 per month.

Oceanfront Beach House with boat dockage Oceanfront Property with brand new Pool

2 bed/2.5 bath townhouse on golf course with shared pool minutes away from downtown Key West, local beaches Indulge in the ultimate getaway experience with our stunning 2 bedroom, 2 1/2 bathroom townhouse nestled on the picturesque Key West Golf Course. Overlooking the lush #1 green, this oasis offers unparalleled tranquility and relaxation. Step outside and immerse yourself in luxury at our lagoon-shaped pool featuring a soothing waterfall - just a few steps away from your doorstep. Unwind in the extended rear yard adorned with vibrant grass and tropical landscaping, creating a serene backdrop for your vacation. Inside, discover a haven of comfort and style. The spacious living room opens up to a screened veranda, perfect for expanding your entertaining space while basking in streams of natural sunlight. A convenient downstairs powder room adds to the convenience of your stay. Upstairs, each bedroom boasts its own private bathroom en suite, providing the utmost privacy and comfort for you and your guests. Experience the epitome of Key West living at our vacation rental - book your stay today and start making memories that last a lifetime. The Key West Golf Club HOA is a gated community offers safe and beautiful paths to run, walk and play. Staying here also gives  you parking for 2 vehicles. Prime Tee Haven, is located at Mile Marker 5 of US 1 and is 1 block from the Key West Hospital, Police Department, Community College and Tennessee Williams Theater. It is about 5 miles from door to door to downtown Key West. This is a pet & smoke free property.

The Crestwood House is a stunning 6-bedroom, 6.5-bath home offers the perfect Key West getaway at Lunara Bay - a collection of 26 luxury homes in a gated community! Enjoy a private pool, fire pit, parking, and a pet-friendly gated yard. Dock your boat at our exclusive marina for boats up to 40’, just steps from your door. Guests enjoy complimentary FYT gym access and personalized itineraries to uncover hidden gems. Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open-concept floor plan seamlessly connects the indoor and outdoor areas, making it perfect for entertaining and spending quality family time. Whether you’re relaxing in the pool, playing a game of pool, grilling delicious meals, or simply relaxing in one of the multiple dining and seating areas, this home has everything you need to create lasting memories. The fully equipped kitchen is ready to cater to your culinary desires, whether you prefer to cook your own meals or hire a private chef. Stay connected with high-speed internet access and enjoy the convenience of keyless entry, making your vacation experience even more seamless and hassle-free. Outside, the spacious fenced-in turf yard provides a safe space for children to play, as well as a perfect area for your furry friends to roam around. The sleeping arrangements of the home are as follows: Bedroom 1: King bed with a walk-in closet, double vanity en-suite bathroom & balcony access Bedroom 2: King bed with a walk-in closet, double vanity en-suite bathroom & balcony access Bedroom 3: King bed with en-suite bathroom Bedroom 4: King bed with en-suite bathroom and balcony Bedroom 5: Two twin over twin bunk beds, this room does not have a door Bedroom 6: Double bed with en-suite bathroom Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level. Travel by car, boat, or plane to our luxury estate. The driveway allows parking for up to 3 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter, moke or bike for the day to explore the area. Feel free to ask us for recommendations! - Private washer/dryer - Located in gated community - Free gym access at FYT

Discover your dream Key West getaway at Lunara Bay - a collection of 26 Luxury homes in a gated community! Floralee House is a 6BR, 6.5BA luxury waterfront estate that seamlessly blends high-end finishes with modern elegance, just minutes from downtown. Dock your boat right in the backyard, unwind in your pool, enjoy complimentary gym access, and enjoy curated itineraries from our local guest experience team. Elevate your visit with our Private Chauffeur Service for effortless transportation. Enter a space where modern sophistication blends seamlessly with tropical style. The spacious living areas are perfect for relaxation or entertaining, illuminated by large windows that let in plenty of natural light. Every bedroom serves as a peaceful retreat, complete with luxurious bedding and private en-suite bathrooms for extra comfort and privacy. The bed layout is as follows: Bedroom 1: King Bed Bedroom 2: Two Bunk Beds with two queen and two twin sized Mattresses Bedroom 3: King Bed Bedroom 4: King Bed Bedroom 5: King Bed Bedroom 6: King Bed All bedrooms have an ensuite bathroom Our self check-in makes the process seamless. Guests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay. Boating & Private Dock Slip: We encourage boating. Here’s what you need to know in order to do so safely: - Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. Travel by car, boat, or plane to Floralee House. The driveway allows parking for up to 2 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Private washer/dryer - Located in gated community. - Free gym access at FYT - Fans inside bedrooms only operate with the light on. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Discover elevated island living at Joyrise House at Lunara Bay, an exclusive collection of 26 luxury residences within a private gated waterfront community. This newly built six-bedroom retreat offers the perfect blend of sophistication and relaxation, featuring a private pool, a private boat dock accommodating vessels up to 50 feet, and expansive indoor and outdoor living spaces designed for effortless entertaining. Enjoy complimentary gym access and personalized itineraries curated by our local Guest Experience Team, ensuring a seamless and unforgettable Florida Keys escape. Extend your stay 7+ nights for 10% off your entire stay! The home’s open-concept indoor and outdoor living spaces create an inviting atmosphere perfect for entertaining and spending quality time with family and friends. Whether you’re relaxing by the pool, grilling the day’s catch, enjoying meals together, or gathering for games and conversation, there’s ample space for everyone to connect and unwind. The fully equipped kitchen is ideal for everything from casual breakfasts to gourmet dinners and can easily accommodate private chef experiences for an elevated culinary experience. Modern conveniences, including high-speed Wi-Fi and keyless entry, ensure a seamless stay from arrival to departure. Outside, the spacious fenced yard provides plenty of room for children to play, pets to roam, and families to enjoy the outdoors together. Sleeping Arrangements Bedroom 1: King Bed with Ensuite Bathroom Bedroom 2: King Bed with Ensuite Bathroom Bedroom 3: King Bed with Ensuite Bathroom Bedroom 4: King Bed with Ensuite Bathroom Bedroom 5: King Bed with Ensuite Bathroom Bedroom 6: King Bed with Ensuite Bathroom Each of the six bedrooms features a king bed and private ensuite bathroom, offering comfort, privacy, and a relaxing retreat for every guest. Our self check-in process is designed to be seamless and convenient. Guests will receive a personalized access code prior to arrival, along with direct contact information for a dedicated local Guest Experience Manager who is available to assist with questions, recommendations, and special requests throughout your stay. Whether you’re arriving by car, boat, or plane, getting around is easy. The driveway accommodates up to four vehicles, with additional space for a boat trailer. Looking to explore the area at a slower pace? Golf carts, scooters, and bicycles are available for rent and offer a fun way to experience the Lower Keys. Want us to handle the booking? Your Guest Experience Manager is happy to assist with transportation arrangements and local rental providers. - Private washer and dryer - Located within the exclusive gated community of Lunara Bay. - Complimentary fitness center access at FYT. - Pets are welcome! Maximum of two pets per stay, with a 40-pound weight limit per pet and a $250 pet fee per stay. - Enhance your stay with our Private Chauffeur Service, offering convenient transportation throughout the Lower Keys and Key West.

*Prior to booking, please note:* Exterior painting project starts on 7/30. The entire project should take 6-8 weeks. Please note that all dates and durations are weather dependent and subject to change. During this time, balconies will be also be painted and the balcony furniture will need to be removed and not available *Please note that this home is available for 28+ night stays only.* This two-bedroom, two-bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean. Enjoy amazing views from this waterfront condo of the sparkling blue waters from your private balcony while relaxing in the tropical breezes and sipping a margarita. Put your feet up and know this is the vacation home you have been looking for. When you enter this waterfront condo, you will find a fully equipped kitchen with everything you need to cook up your fresh catch, dine in the dining area, and relax in the spacious living room that opens to a private balcony with those unlimited ocean views. Pictures do not begin to tell the story of Dune Wind South, this beautifully renovated end unit located in La Brisa Condominiums. Enjoy sunrise ocean views from the large balcony while enjoying morning coffee. Complete with two spacious bedrooms, each with its own full bathroom. A large walk-in closet is great for long stays in your new home-away-from-home, along with ample storage space for all of your necessities. Marble floors are throughout the main living areas, including the balcony and bathrooms. The fully renovated designer kitchen is complete with marble counters, stainless steel appliances, and a temperature-controlled red wine fridge. Dune Wind South evokes luxury style living in the heart of offbeat Key West, offering the best of both worlds. Enjoy walking on Smathers Beach every morning, right across the street from your luxurious condo. Perfect for couples looking to spend a much-needed stay in paradise with the option of having a guest bedroom available for visitors. La Brisa offers your own covered parking space with additional guest parking. A secure gated building, tennis courts, pool, Jacuzzi, clubhouse, and BBQ picnic areas are among the common grounds. Key West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance! Property Manager provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips! *Home Truths:* - Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee. - Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay. - This home has access to a shared pool & hot tub. - This home is part of a gated community. - We allow service animals at this home. If undisclosed pets are brought into the home without Property Manager’s approval there is a fine of $500 per pet. - This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area. - Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. Property Manager is not liable for any guest inconveniences caused due to construction in the area. - Please note that max occupancy includes infants. - Please be advised that documentation may be necessary for ESA/service animals to gain entry. - The elevator is currently out of order. At this time, there is no estimated timeframe for when it will be operational. Parking Details: - 1 covered parking space - All vehicles permitted to park within the La Brisa Community must not be over 20 feet in length, including any attachments to the vehicle, not over 8 feet in width, and not over 7.5 feet in overall height. - Trailers, boats, jet skis, and boat trailers, with or without boats or jet skis, are not permitted in the La Brisa Community. - Kayaks, canoes, and paddleboards are permitted but must be kept on top of the vehicle at all times. - Unauthorized vehicles will be towed at the owner or operator’s expense --- The room configuration is as follows: Primary Bedroom / King bed Bedroom 2 / Queen bed --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at Property Manager than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. We report and prosecute all Credit Card Fraud. Licence number: n/a

Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the pool. Poolside Breeze has an extra large floor plan with an extensive private balcony. Gorgeous new Kitchen renovated in 2018. Both bedrooms and the living room feature sliding glass doors that open on to the private balcony overlooking the lush tropical courtyard of 1800 Atlantic. There is a full size fully equipped eat in Kitchen and a dining room area that seats 6. Full size washer & dryer in the unit. The Master bedroom has a king size bed. The guest bedroom has a queen and for your convenience there is a queen size sleeper sofa in the Living room. The unit has wireless internet. There are Mexican tiled floors in the living room and hallways with carpet in the bedrooms. Enjoy the tranquility that this property has to offer. Minimum length of stay requirement may be in place depending on high/low seasons. For stays shorter than 3 nights please contact the office or email your inquiry. Elevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Southernmost Serenity – Oceanfront 3-Bedroom Condo in Key West Welcome to Southernmost Serenity, a spacious and serene 3-bedroom, 3-bath oceanfront condo offering breathtaking views of the Atlantic Ocean from every bedroom, the kitchen, and the living room. This is the only 3-bedroom, 3-bath direct oceanfront unit in the complex—and the closest to the water—ensuring panoramic views and unparalleled tranquility. Wake up to the sights and sounds of tropical birds, enjoy the lush oasis gardens, and watch boating activities from your private sanctuary. It’s no wonder guests return again and again to this paradise. Prime Location Our condo is centrally located on the Atlantic side of the island: Just 2 miles from Key West International Airport 2 miles from Mallory Square, the island’s vibrant hub of culture and nightlife. Nearby, you’ll find the famous Duval Street, bustling with eclectic shops, lively bars, top-rated restaurants, and fascinating museums. Getting Around Don’t Miss: Mallory Square Sunset Celebration Each evening, locals and tourists gather at Mallory Square for the unforgettable Sunset Celebration. Enjoy: Live street performers and entertainers Unique local vendors And of course, the breathtaking moment the sun dips into the ocean As the sun sets, Key West’s nightlife comes alive. From live bands to the iconic Duval Crawl, there’s always excitement in the air. Stop by Jimmy Buffett’s original Margaritaville, and remember—it’s always 5 o’clock somewhere! Key West Highlights Historic museums World-famous sunsets Vibrant nightlife Incredible seafood and Caribbean cuisine Activities galore: snorkeling, fishing, kayaking, and more This little island may be small, but it’s packed with adventure. So grab your favorite drink and soak up the sun, sand, sea, and fireball sunsets from the best seat on the island—your oceanfront balcony. Cleaning and Safety Practices Your safety and comfort are our top priorities: Professionally cleaned and sanitized between stays Contactless check-in available High-touch surfaces disinfected regularly Ample hand soap and sanitizing supplies provided Come experience the beauty, energy, and relaxation of Key West at Southernmost Serenity. Paradise is calling! Elevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Discover your dream Key West vacation at Lunara Bay - a collection of 26 luxury homes in a gated community!! Springtide House is a 4BR, 4.5BA pet-friendly home blending island charm with modern elegance, just minutes from downtown. Dock boats up to 40’ at private slips, relax in your private pool, access the FYT gym, and enjoy curated itineraries from our local guest experience team. Indulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information! The open concept floor plan makes entertaining a breeze and encourages family time around the dining room table. A fully equipped kitchen awaits your home cooked meals or private chef experience. With high speed internet access and keyless entry vacation has never been more convenient and easy. Sleeping up to 10 guest this home features four king beds and a new sleeper sofa. The spacious fenced in yard and gated dock access are perfect for children and your furry friends. Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival. Boating: We encourage boating. Here’s what you need to know in order to do so safely: - Private dock can accommodate boats up to 50’ in length. Maximum one boat per dock. - There is no power or pump out service to the slips. - The Florida Keys are a notoriously difficult place to navigate. How to Access: Stair access only the home is elevated above sea level Travel by car, boat, or plane to Springtide House, The driveway allows parking for up to 4 vehicles and your boat trailer. If you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. Rent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations! - Extend your stay 7+ nights for 10% off your entire stay! - Elevate your visit with our Private Chauffeur Service for effortless luxury transportation. - Private washer/dryer - Located in gated community. - Comes with free gym access to FYT. - Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$250/stay •2 pet maximum

Beautiful Key West Residence close to Higgs Beach Welcome to the Atlantis House, a beautiful vacation rental located in the heart of the charming island town of Key West. This exquisite property has everything that you could want in a vacation rental home - elegantly designed interiors, high-end amenities, and an unbeatable location close to everything that the island has to offer. The main house of Atlantis House features 3 bedrooms and 2 bathrooms, with elegant modern coastal design elements found throughout. The spacious and beautifully designed open floor plan invites guests to entertain in style, with a large chef’s kitchen boasting high-end appliances that include a huge sub-zero fridge and freezer. Attention to detail and a carefully curated color palette welcome even the most discerning traveler, creating an atmosphere of laid-back luxury that is perfect for your island getaway. One of the highlights of Atlantis House is the bonus second-floor bedroom, which boasts stunning ocean views and offers yet another option for dining and entertaining. The nice upstairs terrace is the perfect spot to relax with a book or enjoy an evening cocktail, taking in the sights and sounds of this vibrant island community. The location of Atlantis House is truly unbeatable - located just steps from the Whitestreet pier and within walking distance of Higgs and Smathers Beach, which are two of the most popular beaches on the island. Additionally, the nearby farmers markets and free bikes provided by the property make it easy to explore and experience everything that Key West has to offer. If you are seeking a monthly vacation rental that truly embodies the essence of island living, then Atlantis House is the perfect choice. With its unbeatable location, elegant design, and thoughtful amenities, this vacation rental is a true island gem. We invite you to come experience the best of Key West living at Atlantis House.

Mermaids Retreat | Spacious Key West Vacation Rental with Pool, King Suites & Full Kitchen Welcome to **Mermaids Retreat**, a spacious and inviting **Key West vacation rental** located on beautiful **Stock Island**, just minutes from the excitement of Old Town Key West. Whether you’re planning a family vacation, couples’ getaway, fishing trip, or extended stay, this island retreat offers the perfect combination of comfort, convenience, and tropical charm. Relax in Comfort Designed with relaxation in mind, Mermaids Retreat features a fully equipped kitchen, a comfortable dining area, and a bright living space that’s perfect for gathering after a day of exploring the Florida Keys. Enjoy your morning coffee on the front porch or unwind with an evening cocktail on the back porch while taking in the warm island breeze. Spacious Accommodations This three-bedroom home comfortably accommodates families and groups. **Main Floor** * One comfortable guest bedroom * Full bathroom * Open living, dining, and kitchen area **Second Floor** * Two spacious king bedrooms * Two private en suite bathrooms * Large open-air balcony perfect for relaxing For added convenience, the home also includes a stack-able washer and dryer, making longer stays easy and comfortable. Resort-Style Amenities Guests enjoy access to the community amenities located just steps away, including: * Community swimming pool * Clubhouse * Fitness center * Parking for up to two vehicles in a nearby outdoor lot Explore Stock Island & Key West Mermaids Retreat is perfectly situated to enjoy the authentic charm of Stock Island while remaining just minutes from world-famous Key West attractions, beaches, marinas, shopping, and nightlife. Some local favorites nearby include: Roostica – Popular for authentic wood-fired pizza and Italian cuisine. Hogfish Bar & Grill – A beloved waterfront restaurant serving fresh local seafood. El Siboney Stock Island – Authentic Cuban cuisine and local favorites. The Docks Seafood Market– Fresh, locally caught seafood to take home. Croissants de France – Located directly across the street for fresh pastries, breakfast, coffee, and sandwiches. The Perfect Florida Keys Getaway Whether you’re fishing offshore, exploring the waters by boat, visiting Key West’s historic attractions, or simply relaxing by the pool, **Mermaids Retreat** provides everything you need for an unforgettable Florida Keys vacation. Highlights * Minutes from Old Town Key West * Three spacious bedrooms * Two king suites with private bathrooms * Three full bathrooms * Fully equipped kitchen * Community pool and fitness center * Private outdoor porches and balcony * Washer and dryer * Parking for two vehicles * Close to restaurants, marinas, fishing charters, and local attractions Book your stay at **Mermaids Retreat** and experience the best of Stock Island and Key West from the comfort of your own tropical retreat.