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Holiday rentals in Boot Key Harbor

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Top-rated holiday rentals in Boot Key Harbor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A two-story house is surrounded by lush greenery and palm trees. A spacious backyard features a heated pool and a wooden dock. Loungers are arranged near the pool, providing a relaxing outdoor space. The exterior showcases large windows and a balcony with seating.
Home in Marathon
4.98 out of 5 average rating, 87 reviews

Sombrero beach vacation paradise, great location

Your family will be close to everything when you stay at this centrally-located home. Close to Sombrero beach you can walk ride a bike, kayak or take a short drive there. Many attractions near by. Publix and winn dixie and many restaurants near by. Key West just one hour away for any day trip. House has an ice maker, refrigerator and freezer downstairs to keep bait or fish .Private pool and Dock, back yard oasis There is a paddle board and 4 bikes and 2 kayaks for your use. Amazing location!

Superhost
Houseboat in Marathon
4.77 out of 5 average rating, 151 reviews

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

Guest favourite
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.
Home in Marathon
4.94 out of 5 average rating, 35 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.

Guest favourite
A light blue house is prominently featured, elevated above ground level with a staircase leading to the entrance. Palm trees surround the property, creating a tropical ambiance. Nearby homes display a mixture of colors, enhancing the neighborhood's coastal charm.
Home in Marathon
4.87 out of 5 average rating, 31 reviews

Sombrero Beach Getaway

Spend your days boating, fishing, and swimming in the South Florida sunshine when you escape to this waterfront home in Marathon! Scenically, this home features a 90 -foot dock (with a filet cleaning table and water), a private heated outdoor pool, and a patio where you can grill your fresh catch each evening. We are located just minutes away from restaurants, bars and entertainment. Key West is less than an hour from the property. We can provide help with Golf Cart and Boat rentals.

Guest favourite
Home in Marathon
4.88 out of 5 average rating, 17 reviews

P98 - 75ft dock with shore power, 4 bed, 4 bath ho

75-foot dock with shore power 30 and 50amp This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style with extra attention given to each and every detail. This property is warm and inviting and located in the desirable neighborhood of Sombrero Beach. This home is perfectly positioned on the property to maximize full use of the grounds, providing ample parking in the front, while creating an abundant outdoor living space in the back.

Top guest favourite
An inviting outdoor area features a clear swimming pool surrounded by a paved patio. The two-story structure above includes spacious balconies with multiple seating options. Sunlight brightens the scene, and lush greenery is visible in the background, enhancing the tranquil environment.
Home in Marathon
4.97 out of 5 average rating, 114 reviews

Angler's Eden

Amazing get-away in the beautiful Florida Keys! This property (constructed in 2018) is a haven for families seeking to escape to paradise year-round. Situated on a deep water canal with ocean access and enough dock space to park your boat for the week. A floating dock is also provided with kayaks. Enjoy the large pool or ping pong table, or lounging in the sun! Beautiful Sombrero Beach is within walking distance (approx 1.5 miles) via a paved bike path.

Top guest favourite
Home in Marathon
5.0 out of 5 average rating, 26 reviews

Villa Serenity At Sombrero Private Pool Spa Dock

Relax and unwind at Serenity at Sombrero! This cozy canal front vacation home is perfect for a secluded and relaxing Florida Keys getaway! The three bedroom two bathroom, newer build stilt home comes fully apportioned with a 30' concrete dock with space for up to a 45' boat, optionally heated pool and spa, and large industrial sized ice machine! Centrally located and just minutes from Sombrero Beach and all major shopping and tourist attractions!

Top guest favourite
Flat in Marathon
5.0 out of 5 average rating, 31 reviews

Waterfront Suite | Pool & Tiki Bar

Stay at Mystic Mermaid, a brand-new luxury 1BR/1BA Waterfront Villa that sleeps up to 4 guests. Located on a scenic canal in the heart of the Florida Keys, this elegant retreat offers marina views and resort-style amenities including a pool, Tiki Bar, restaurant, pickleball & sand volleyball courts, fitness center, and complimentary breakfast. Perfectly located between Islamorada and Key West for the ultimate island getaway.

Guest favourite
Home in Marathon
5.0 out of 5 average rating, 10 reviews

A Paradise Point by Sombrero Beach

Modern Tropical Paradise | Marathon, FL Stylish home in exclusive Flamingo Isle, minutes from Sombrero Beach, marinas, fishing piers, indoor surf-style shop, and the Florida Keys Country Club. 3 bed | 2 bath + den Downstairs full bath with handicap-accessible walk-in shower Living room + playroom (pool table, games) Outdoor: Heated pool , Jacuzzi, BBQ, tiki hut Corner lot with parking for boat trailer & RV (full hook-ups)

Superhost
A private plunge pool is framed by stone flooring, with a landscaped area featuring potted plants nearby. The spacious outdoor space is complemented by a covered seating area and large sliding glass doors leading into the home.
Home in Marathon
5.0 out of 5 average rating, 4 reviews

Bayside Boaters Paradise w/Pool – Marlin Bay

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Top guest favourite
Home in Marathon
4.94 out of 5 average rating, 205 reviews

70ft Dock, Bikes, Beach, Spacious, VACA23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

Top guest favourite
Home in Marathon
4.97 out of 5 average rating, 38 reviews

Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool

Make memories of a lifetime in Sombrero Beach, Martathon in the Florida Keys. 7 bedrooms (6 King Beds), 6 full baths, 80' dock, private pool, fenced yard, parking for 6 vehicles plus two boat trailers. Only minutes from the Atlantic Ocean and Gulf of Mexico. Enjoy world class fishing and diving. Sombrero Beach is stunning and only a mile away. Beautiful neighborhood with golf course views from the front.

Popular amenities for Boot Key Harbor holiday rentals