Holiday rentals in Boot Key Harbor

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.

Value · Family · Amenities

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.

Family · Location · Comfort

Private Pool, Kayaks, Deep Water Dock, Near Golf

Salt Cottage Sombrero Tucked away in Marathon’s exclusive Flamingo Island neighborhood, this stunning 3-bedroom, 2-bath waterfront retreat offers the perfect blend of island charm, coastal luxury, and outdoor adventure — complete with a 30’ dock (Boat lift is not for Guest use), private pool, and thoughtful amenities. *Pets are considered on a case by case basis and only after a paying a pet fee. Please do not book this home if you plan on bringing a pet without checking with us first

Location · Family · Pets

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Value · Family · Outdoor spaces

*NEW* Reel Escape~50'Dock!~Pet Friendly~Grill!

Welcome to Marathon, FL, the heart of the beautiful Florida Keys 🌴 This charming 3BR, 2BA coastal retreat features a private 50' dock, perfect for boating and water adventures. 🚤 Rent a boat or bring your own! Enjoy rare single level ground floor living with easy access from parking to the entire home, backyard, and dock. Relax in outdoor spaces, cook in a fully equipped kitchen, and unwind in comfort. Minutes from Sombrero Beach, dining, and more ☀️ 🐾Pets welcome!🐾

Grill · Pets · Kitchen

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.

Location · Family · Pool

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

🏝️ <b>Oceanfront Luxury</b> - Brand New $4M, spacious 5-bedroom, 4.5 bath home 📍 <b>Prime Location</b> - Minutes from Sombrero Beach, top restaurants, island bars, and boutique shopping 🔥 <b>Free Heated Pool</b> - Gorgeous ocean views ⚓️ <b>Private Marina Access</b> - 38 ft protected boat slip 🏈 <b>NFL Sunday Ticket Included</b> - Catch every out-of-market Sunday game during your stay ✅ <b>Hassle Free Checkout</b> - No chores, no stress. Just pack and go.

Location · Value · Checkout

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.

Location · Family · Accuracy

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!

Family · Location · Nearby

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)

Location · Kitchen · Indoor spaces

Marina View Villa | Dockfront, Pool & Tiki Bar

Sassy Seahorse is a brand-new waterfront villa in Marathon, FL—perfect for a relaxing Florida Keys escape. This luxury 1BR/1BA retreat comfortably sleeps up to 4 guests and features a plush king bed, spa-inspired bathroom, stylish living area with sleeper sofa, and a fully equipped gourmet kitchen. Enjoy peaceful marina views from your private patio and soak in the laid-back island lifestyle in the heart of the Keys.

Family · Location · Nearby

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.

Family · Value · Comfort