Holiday rentals in Raccoon Key

3BR In Resort Village, Pools, Free Kayak & Shuttle

Experience the ultimate KEY WEST VIBE aboard our 3BR/2BA sailboat Located at the luxury Perry Hotel, you’ll enjoy on water living, palm trees, and salty air. Free Perks: Kayak, pools, parking, & free shuttle to Old Town! Full Resort Access: 2 pools & hammock park, 3 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Plz read everything below before booking. I want you to be completely informed about staying on the water. We look forward to hosting you! 🌊💙⚓

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.

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.

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.

Stella on Stock Island

Perched on the shimmering waters, this 1 bedroom, 1 bath houseboat epitomizes cozy waterfront living. Step inside and you'll find yourself welcomed into an inviting living space. The living area transitions into a kitchen complete with essential appliances. Down the hall from the living area lies the bedroom offering a peaceful haven for rest and relaxation after a day spent exploring. An elegantly appointed bathroom awaits, featuring modern fixtures and amenities. Queen Bed & Sofa Bed

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.

Funky Chicken Cottage with Shared Pool in Paradise

Funky Chicken Cottage is a charming and eclectic vacation rental located in Key West, just a short drive away from the main island on Stock Island, Florida. This 3 bedroom, 3 bathroom property is the perfect blend of comfort and style, with unique Martha DePoo art and Cuban art. The highlight of this property is the beautiful pool area, gated community. The property also features two parking spaces under the house, making it convenient for guests who are driving to the island.

Love Shack: 2BR Houseboat w/ Decks & Views

Escape to Love Shack, our renovated 54-ft 1979 Stardust Cruiser houseboat. Great for couples, small families, or up to 4 guests. Wide water and mangrove views from the back deck are perfect for sunsets and stargazing. Primary bedroom has a queen bed with water views. The second bedroom has a small RV-size pull-out couch. Full bath and kitchen included. Two decks for relaxing: back deck with table and chairs, upper sundeck with lounge chairs. About 15 minutes to Duval Street.

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.

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.