Villa vacation rentals in Stock Island

Harbor hideaway 50’dock 3Br/2Ba All amenities

VACA-23-42 is a charming villa that perfectly serves as your cozy retreat, featuring a private saltwater pool right by the water’s edge. There’s ample space available for your boat, trailer, and several vehicles. Enjoy our bicycles and kayaks during your stay. The property also boasts a tiki hut equipped with a commercial ice machine, grill, and a fish freezer for all your fishing needs. This unique getaway is conveniently situated near all local attractions, making your trip planning a breeze.

"Keepin’ It Reel" Waterfront, 4BD/3BA FL Keys Home

This stunning home on the Intracoastal Waterway is loaded with amenities including: private pool, patio, boat dockage, a large balcony, a spacious & updated interior that accommodates up to 10 guests. A perfect rental home for you, family & friends to enjoy for a relaxing vacation. When you need to book 3/4 rooms for the family, you can book this 4-Bedroom Villa w/ a full gourmet kitchen. Nestled 10 minutes away from the iconic Sombrero Beach. Close by enjoy various restaurants, shopping & more.

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Howard House on the Sea

Oceanfront coastal elegant 10.5 feet from door to ocean with an extraordinary, unobstructed view of sunrises. Dock your 30’ boat here. Designed to make you feel like it’s your home from the minute you walk in the door. Fresh,clean and fabulously landscaped. Gourmet kitchen. Kayaks. Pool. Hot tub, tennis/pickle ball courts, washer/dryer, high speed internet and smart TV. Only 20 minutes north of key west. Fish off the dock! $100 gift card to Square Grouper or Broils for 7 or more night stay

Discount to Jan 31! Outdoor TV! Lots of Amenities!

This beautiful 4 bedroom, 3 bath home (duplex) is less than 2 minutes from Sombrero Beach just down the street (oceanfront) and less than 15 minutes to open water! The living room has a sleeper sofa (linens provided). Private pool with outdoor tv on the patio, dock (shared with unit 2), 2 bikes, 2 kayaks, 2 paddleboards, bait freezer, gas grill! Private dock that can accommodate up to a 30' boat. Four parking spots for your cars and boat trailer (covered parking for 2). Only ONE boat allowed.

5% Off Thru January - 4Bed 3Bath! Tiki Hut w/ TV!

Dockside Retreat! Rent one side or both! This 4 bedroom 3 bath canal front home has a private pool, private dock, fish cleaning station, green light under at the dock, two kayaks, two bikes, and a Tiki Hut for the ultimate Keys vacation! With plenty of parking for vehicles and a boat trailer, a well-stocked vacation rental with everything you need, a neighborhood beach just down the street and located at mile marker 55, in the heart of Marathon, Dockside Retreat is your perfect vacation spot!

Sol Island ~ Waterfront Oasis ~ Pool ~ Dock ~ Kayaks

Indulge in this luxurious 4BR 4BA house nestled on a gorgeous waterfront property in Marathon, FL. This 3-story estate offers the perfect retreat from bustling crowds with its modern design, high-end comforts, and scenic outdoors with heated pool, private dock, rooftop deck, and Pac-Man arcade. ✔ 4 Comfortable BRs ✔ Open Design Living ✔ Chef's Kitchen ✔ Heated Pool ✔ Yard (BBQ, Games, Bikes, Kayaks) ✔ 36ft Dock (Fishing Station, Water) ✔ 3 Decks ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking

Discount Available-Pool/Dock/Bikes/Local Beach

WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES! "SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath pool home (and sleeper sofa) with neighborhood Ocean Front beach just down the street! The private pool that can be heated or chilled, private dock (up to 35' boat), fish cleaning station and 4 bikes! Fully stocked home and kitchen with everything you need included! Free WIFI! Centrally located in Marathon, just an hour from Key West!

(#4)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

#4: A WAVE💦 FROM IT ALL (Partial Ocean View Property-approximately 150 ft from beach entrance)🌸 Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming Pool 🤿and BBQ Patio. Includes Private Guest Beach🏖 with Kayaks and Paddle boards and Private powered ⛵Boat Dock right on the Gulf of Mexico! 🌅🥂 Kick back and completely🍷 relax in our Beautiful and 🍹comfortable home! Perfect for 🍻Adults and kids of all Ages!

Marathon Villa w/ Priv Pool/Dock

Marathon, Florida is in the middle of all the beauty and action of what the Florida Keys have to offer. Sombrero Beach is at a bike ride or walking distance. It offers complimentary parking, outdoor grilling, beach volleyball, children play area, and public restrooms. 40 foot dock offers guests the option to bring their boats or rent one. Our heated pool is a perfect way to soak up the tropical vibes. Kitchen is fully equipped. We are at walking distance to grocery store!

Discount to Jan 31! Private Pool, Fun Amenities!

This property has everything! 4 bed, 3 bath, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! The dock is shared with the unit next door. One boat only is allowed. Limited parking. 2-3 cars with trailer max. The pool can be heated for a fee of $ 150 plus tax, processing. Prorated for longer stays.

Beachfront • Heated Pool • Hot Tub • Oceanview

Welcome to your slice of paradise in Cudjoe Key! This two-story Oceanview villa combines tropical serenity with modern comfort, perfect for families, couples, or friends. Enjoy a private heated pool and spa, spacious living areas, and breathtaking Atlantic views from the master suite. Whether you’re exploring Key West or relaxing under the sun, every moment here feels like pure vacation bliss.