Holiday rentals with a fire pit in Vaca Key

5 out of 5 average rating, 12 reviews

Oceanfront Rooftop Views w/ 75ft of Dockage

Welcome aboard Captains Rooftop, Your 4BR Rooftop Deck Hot Tub Oasis on a direct ocean access canal with 75ft of dockage. This three story stilted rooftop home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ 2 Luxury jet Hot Tubs (One on the roof, one in the backyard) ⛵ Private 75ft dock surrounded by a mangrove jungle 🕹️ Foosball Table 🍳 Rooftop patio with BBQ grill & open ocean view dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

4.97 out of 5 average rating, 100 reviews

A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.

Cottage in Islamorada

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

A sandy beachfront is framed by palm trees, with the glistening Atlantic ocean in the background. A volleyball net is set up on the sand, along with multiple seating areas for relaxation, inviting guests to enjoy the tranquil environment and scenic views.

4.92 out of 5 average rating, 49 reviews

Viamarhe House-Private beach, Kayak, yard games

If you are looking to enjoy the natural beauty and the captivating views of the Florida Keys, our charming Oceanfront house is the place for you. Enjoy the breathtaking views of the sunrise and the starry night show over the beautiful Atlantic ocean. You and your family can enjoy the exclusivity this property will give you, Viamarhe is its own little resort, 5 kayak and fishing rods, volleyball, chess and bowling ground, Domino, Billiards, Ping-Pong, and Football. the propane BBQ grill, fire pit

4.97 out of 5 average rating, 138 reviews

A serene pool area is framed by lush palm leaves, highlighting a sparkling pool with a bubbling spa. Sun loungers are arranged around the pool, complemented by a large blue umbrella providing shade.

Cottage in Islamorada

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

A clear view of a swimming pool framed by lush greenery and manicured grass, extending toward the Atlantic Ocean. The tranquil water reflects the blue sky above, enhancing the serene setting.

4.88 out of 5 average rating, 17 reviews

SAY'S BY THE SEA

Oceanfront 2BD/2BA and separate 1BD/1BA pool-side overlooking the Atlantic* Enter your paradise dream home with stunning views and privately nested away from the big city noise. You'll be staying in our large three bedrooms and three baths secluded retreat with a large terra overlooking the Atlantic Ocean. The home's rooftop deck on the third floor offers a panoramic and open observatory which is great for catching rays, watching sunrises, sunsets and shooting stars. RENTAL LICENSE #VACA-22-30

A two-story home is showcased, featuring a spacious backyard with a swimming pool surrounded by lounge chairs and umbrellas. The exterior is illuminated under a twilight sky, while a stone walkway leads to the inviting entrance. Lush greenery adds a vibrant touch to the setting.

5 out of 5 average rating, 50 reviews

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Experience the relaxing setting of this 4BR 4.5Bath home, ideally situated in the picturesque waterfront neighborhood of Marathon, FL. Discover the area's scenic beauty and a diverse selection of water activities, attractions, and landmarks. After a day of exploring, return to our home for a rejuvenating stay. ✔ 4 Comfy BRs ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Backyard (Pool, Games, BBQ, Lounges, Dining) ✔ 73-Foot Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

4.93 out of 5 average rating, 88 reviews

A spacious living area features a comfortable blue sofa and a white coffee table at its center. Modern appliances are visible in the adjacent kitchen, along with a dining area. Natural light flows in through sliding doors leading to the outdoor space.

Holiday home in Marathon

Perfect Paradise

Perfect paradise is located in the heart of marathon. Only 9 minutes away from sombrero beach. Restaurant, supermarkets, ice cream, aquarium, and much more less than 7 minutes away. Public boat ramp is 5 minutes away. The house has plenty of parking spaces in the front to park your boat and cars. The home is fully stocked with everything you will need during your stay. For specific dates please message me first before booking so I may accommodate you to the dates that you would like to book.

A stilted beach house stands beside a serene canal, with lush green foliage lining the wooden dock. A kayak rests on the dock, while palm trees sway gently in the background, all under a bright blue sky.

4.93 out of 5 average rating, 30 reviews

Walk to Sombrero Beach, 50’Dock, SPA, Kayaks,Bikes

Cozy FL Keys stilted beach house ideally located in Sombrero Beach w/ 50’ private dock & large SPA whirlpool & attached bar. Walk/bike to beautiful Sombrero Beach down paved path. 4 bikes, 2 paddle boards, 2 kayaks included. Renovated home with new central A/C unit, new bathrooms & kitchen. Near supermarkets, liquor stores, pharmacy, great restaurants & more. Near Dolphin Research, Aquarium Encounters, Turtle Hospital, Bahia Honda State Park Beaches & more. Key West less than 1 hour away.

A tropical backyard features a private saltwater pool surrounded by seating areas. A thatched-roof Tiki Hut is adorned with string lights. A gas fire pit sits centrally, while walls are embellished with colorful fish murals. Lush greenery completes this inviting outdoor space.

4.93 out of 5 average rating, 107 reviews

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!

Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

Superhost

The outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.

4.88 out of 5 average rating, 86 reviews

Gorgeous Ocean View Home!

Beautiful family friendly ocean view home centrally located in the heart of Marathon (only 10min from Sombrero Beach) were you’ll be able to do many things like snorkeling, fishing, boating, Scuba, museums, visit the aquarium, and/or the dolphin research center, and even dine on the water with many restaurants selections near by. This property does NOT have dock space for a boat or trailer parking. Licensed and inspected by the city of Marathon Lic.# VACA-23-144

5 out of 5 average rating, 7 reviews

Lux Waterfront: Dock, Volleyball, Putt Putt, More

Pescayo Pointe Welcome to your modern Florida Keys escape—an upscale 4-bedroom, 3-bath canal-front home designed for comfort, entertainment, and effortless access to the ocean. This newly built property blends tropical elegance with resort-style amenities, making it perfect for families, couples, and avid boaters. Step into a bright and inviting living space adorned with coastal accents and designer touches. 4 bedrooms | 6 beds | 3 bathrooms