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Seagrass-Free • New 5BR Pool Home w/ Ocean View

Brand new build 2024. This 5 bed/4bath luxury ocean gulf home with boat dock, heated/chilled pool/ spa, paddle boards kayaks, bicycles was meticulously designed and custom built like no other house in Marathon Key. You can see ocean water from every room in the house. and the interior design was chosen to maximize comfort, with a stress-free peaceful setting. Only three homes on this one-acre private ocean gulf lot that has the look and feel of a private island with 400 feet of bulk head

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Ocean Front 2-bed 2 Bath in beautiful Key West

Hyatt Windward Pointe Resort, Key West -- unit 5211: Family friendly 2-bedroom condo, sleeps up to 6 people, has a full kitchen, an outdoor terrace with ocean view. Beautiful pool with outdoor grill area and play courts. Available only for arrival Saturday February 7 thru departure on February 14, 2026. Wi-Fi available to all throughout resort with full 1 gig rates for both uploads and downloads. The entire resort property-size available to all resort guests is approximately 90,000 square feet.

Cathouse Old Town Tropical Oasis Huge Pool/Parking

Relax in this tropical poolside townhouse in the heart of Key West hosted by Nautipussy! Wake up surrounded by lush tropical landscaping and enjoy morning coffee on balconies overlooking the pool. Three levels provides for unparalleled privacy. Shopping and restaurants are within walking distance, prepare a gourmet meal in the fully equipped kitchen, or grill poolside. Take a dip in the pool or walk to the beach. Feel secure in the gated 3 unit mini compound with covered off street parking.

Tiny House | 35 min to KW + Free Parking & Pool

Discover a hidden gem in the Florida Keys with this charming Tiny House, surrounded by nature and the famous Key Deer. Located in the peaceful Breezy Pine RV Resort, it offers a cozy yet spacious layout for the whole family. Relax outdoors on the private patio with sofa and grill, perfect for enjoying the laid-back Keys lifestyle. With all the essentials for comfort and just a short drive to Key West, Bahia Honda beaches, shops and restaurants. This retreat is ideal for relaxation and fun.

The Twin Palm Villas - B

Indulge in island luxury at this stylish 2BR/2BA canal front oasis just blocks from Sombrero Beach. Located in a newly renovated duplex, this light-filled unit features coastal-modern design, plush bedding, a chef-ready kitchen, and a breezy outdoor patio overlooking the water. Wake up to tranquil canal views, or stroll to the white sands of Sombrero Beach. Whether you’re here to relax, boat, fish, or explore, this upscale hideaway delivers serenity and style in the heart of Marathon.

Hemingway First Floor Townhouse @ Suite Dreams Inn

Suite Dreams Inn is an intimate family-owned boutique Key West Bed & Breakfast in the tranquil upscale Casa Marina Old Town neighborhood, offering oversized suites with luxurious king & queen beds, kitchens, living rooms, 2 pools, 24/7 laundry, free parking, and relaxing outdoor spaces. We are LGTB & pet friendly & will accommodate well behaved children of any age, as well as private clothing optional & traditional guests. Close to the beach, Duval St., jet ski r

Stunning Townhouse * Full kitchen! * Sleeps 6

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 21/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all!

3-Bed Oasis in Midtown Key West

Experience the best of Key West in this fully renovated 3-bedroom, 3-bathroom home, where modern convenience meets tropical charm. • Sleek Interiors: Enjoy quartz countertops, high-end appliances, and the convenience of indoor laundry. • Outdoor Bliss: Relax or entertain in a fenced astroturf yard with a shaded dining area beneath stylish shade sails. • Added Perks: EV charging station, off-street parking, and onsite storage for your essentials.

Signature King

Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West. On property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise. Don’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.

Duval Street Suites with full kitchen heated pool,

Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duval street in historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

Oceanfront Condo in Key West

Key West Beach Club is a serene waterfront oasis located in an upscale gated community within walking or biking distance to the local’s finest spots, including restaurants, beaches, shopping centers, bars and the infamous Duval Street. This complex prides itself for being one of the very few on the island that sits directly on the water.