House vacation rentals in Key West

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Gorgeous Romantic Private Villa, Steps from Duval!

Located 20 yards from historic Duval St in the heart of Old Town Key West w/ free ... first-come, first-serve PARKING in front (4 spots). Totally remodeled, beautiful spacious & private 2 story villa sleeps 4 comfortably. New furnishings, free hi-speed wifi, 65" smart tvs, ice machine, electric fireplace in large master suite, lush garden courtyard & shared plunge pool. We provide 2 coffee/tea stations. Walking distance to everything - convenience store, CVS, bars, restaurants & entertainment.

Location · Value · Access

Duval Vibes • Pool • 10 Guests

Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.

Location · Value · Checkout

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Guest favorite

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Family · Value · Backyard

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Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Location · Family · Check-in

Key West Paradise

Bring the whole family or a great group of friends to this fantastic house w/lots of room for fun. 3 Bed (1 on main level, 2 up), 3 Full Baths (1 on main level, 2 up), sleeper sofa in living room and air mattress in closet, Steps to Community Pool, Sleeps up to 8. Nice Kitchen for your use. High speed internet. TV in the living room and in every bedroom. Enjoy the breeze from your nice size front porch, rear deck off living room, and balcony off upstairs bedroom. 8 minutes to Duval Street.

Location · Family · Amenities

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

Family · Location · Hospitality

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

Value · Family · Backyard

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Guest favorite

Private Pool Tropical Oasis - Centrally Located

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

Family · Location · Condition

Waterfront Anchor House with Boat Basin & Ramp

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Family · Location · Hospitality

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Guest favorite

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 · Check-in

Paradise found

Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.

Location · Value · Decor

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

Charming 3-Bed, 3-Bath Home in Gated Community Spacious standalone home with stunning views of the free-form pool. Enjoy the breeze from your private porches in a secure, peaceful setting. A perfect blend of comfort and privacy!

Value · Family · Checkout