Holiday rentals in Middle Keys

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The Sanchez House Room #2

There is no better welcome to Key West than staying in local and famous folk artist Mario Sanchez's birth home. This home was built in the 1860's in the heart of the historic Gato and Merrero cigar factory villages. Featuring original Dade County pine construction, and located right on historic Duval Street, the Sanchez House is guaranteed to offer the historic atmosphere and living a part of Key West many visitors want to experience. Sit on the balcony and enjoy the trade winds & Ocean Breeze.

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

Serenova - 58' Leopard Catamaran

Wake up to gentle waves aboard Serenova, a luxurious 58' Leopard catamaran docked at Stock Island Yacht Club. Enjoy the spacious salon, private cabins, full galley, and expansive decks with panoramic water views. Guests have access to the marina pool, beach, tiki huts with hammocks, gym, laundromat, and free parking right by the boat. Just minutes from Key West’s best dining, sunsets, and adventure. Your private floating home in paradise—create unforgettable memories without leaving the dock.

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Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Grand Marina Suite - Poolside & Waterfront Condo

A beautiful oceanfront suite located at the best marina in the Keys. Situated on the glistening Atlantic Ocean, our Grand Marina Suite is a tranquil respite with on-site access to boat dockage and world-class fishing charters. Located minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel.

Signature King at Beachside Resort

Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West. On property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise. Don’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.

“The Easy Way” Comfy, Practical, Convenient

Reconnect with nature at this unforgettable escape. Stay off Key West away from the crowds and listen to nature. Vessel “Easy Way” is perfect for up to 2 people. Come enjoy the amazing sunrise and sunset. Cook out on the balcony, watch fish, birds, stingrays, and dolphins go by. Vessel Easy Way has an outdoor shower, paddle board, and outdoor grill. This floating home is perfect for people who want to relax and enjoy nature.

Waterfront Boat Stay + Resort Amenities

Docked at the exclusive Perry Hotel & Marina, this 40-foot, 2-bedroom luxury yacht is tucked away from the crowds, while remaining just minutes from downtown Key West. Featuring inviting indoor and outdoor spaces for living, dining, and relaxing, it offers the perfect balance of comfort and adventure. Guests enjoy hotel amenities, including two pools, a gym, and three waterfront bars and restaurants.

Tiki Suites ~ Original Tiki ~ Floating Bungalows

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

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.

Top guest favourite

Guest favourite

Wake Up On The Water | Luxury Marina | Key West

Wake up to the rhythm of the water and experience Key West from a completely different perspective. Stay aboard a 45-ft sailing yacht at the Perry Hotel & Marina. Enjoy 2 pools, gym, fine dining, and a free shuttle to Old Town. Ideal for couples or close knit groups: intimate, memorable, and all part of the yacht lifestyle.