Vacation rentals in Raccoon Key

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Top-rated vacation rentals in Raccoon Key

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Top guest favorite

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

Home in Key West

4.95 out of 5 average rating, 358 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Guest favorite

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

Boat in Key West

4.91 out of 5 average rating, 200 reviews

Stay on Roxie with FREE anytime cancellation!

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Superhost

A three-story historic building is framed by palm trees and tropical foliage. White decorative railings and an ornate archway lead to the entrance, while soft sunlight brightens the exterior's yellow siding. The inviting architecture complements the serene surroundings.

Vacation home in Key West

4.86 out of 5 average rating, 336 reviews

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Superhost

A bright living room features a light gray sofa and a glass coffee table, with a wall-mounted flat screen TV displaying a beach scene. Large windows provide views of the waterfront, while ceiling fans circulate the air, enhancing the spacious ambiance.

Condo in Key West

4.81 out of 5 average rating, 188 reviews

Old Town "Eleuthera" • 2BR Waterfront Corner Condo

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. More space, more comfort, Key West done right. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, buiding elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

Top guest favorite

A spacious swimming pool is surrounded by lush tropical greenery and lined with lounge chairs. Tiki-style huts provide shaded areas for relaxation, while the pool's clear blue water reflects the vibrant sky, creating a serene and inviting environment.

Home in Key West

5 out of 5 average rating, 25 reviews

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.

Superhost

A tranquil outdoor pool is surrounded by palm trees, with lounge chairs and tables positioned for relaxation. Umbrellas provide shade near the water, while a charming cottage can be seen in the background under a clear blue sky.

Townhouse in Key West

4.86 out of 5 average rating, 203 reviews

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

Superhost

A tranquil marina scene is captured at sunset, with colorful clouds reflecting on calm water. A row of Aqualodges is visible along the water's edge, alongside several parked boats and a tiki hut, creating a serene atmosphere.

Houseboat in Key West

4.72 out of 5 average rating, 244 reviews

Deluxe Bungalow

Hurricane Hole Marina offers dual single stateroom Aqualodges for nightly and weekly rentals. Each Aqualodge has a kitchenette, living room, 2 bedrooms, a loft, and a pull out couch. Fire TV, WIFI, and A/C. Check in 3:00PM and Check out 11:00 AM. Waterfront bar and restaurant, Boat rentals, jet ski, kayak, paddle board rentals, tikis, Sandbar and fishing and diving charters, ship store . No smoking. Free parking available on a first come first served basis.

Top guest favorite

Boat in Key West

4.87 out of 5 average rating, 156 reviews

All Inclusive! Snorkel • Sail • Sun & Fun

Stay aboard our 42’ Lagoon 420 catamaran anchored off downtown Key West. Hosted by Captain Dan, a 10-year Superhost, your all-inclusive stay includes snorkeling, sailing, spear fishing, and fishing gear. Relax in the private queen cabin with ensuite bath, enjoy the fully equipped galley, and unwind in the air-conditioned salon. Quick dinghy rides bring you to Key West’s vibrant dining and nightlife. Your perfect floating island escape!

Guest favorite

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

Apartment in Key West

4.9 out of 5 average rating, 151 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

Superhost

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.85 out of 5 average rating, 257 reviews

Key West Luxury Houseboat at Yacht Club Resort

PANORAMIC Ocean Views - POOL 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, 500 square foot Rooftop Sky-Deck - 2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV, 42 inch TV, 32 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

Guest favorite

A bright and airy living area is filled with natural light from large windows offering expansive water views. A comfortable light blue sofa and a matching armchair provide seating. A decorative coffee table sits in the center, and tropical plants are visible outside.

Townhouse in Key West

5 out of 5 average rating, 12 reviews

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.

Guest favorite

A serene pool area is surrounded by lush tropical palm trees and vibrant landscaping. Sunlight reflects off the clear water, creating a calming ambiance. Nearby, a white lounge chair is positioned for relaxation, with a life preserver visible on the side.

Home in Key West

4.9 out of 5 average rating, 111 reviews

Gone Coastal

Relax with the whole family at this peaceful place to stay. Completely renovated 3 bedroom 2.5 bath townhome in Coral hammock. Enjoy the pool and excellent location on Stock island. Walking distance to Roostica and Hogfish grill. Dogs are welcome but not over 25lbs. Pitsbulls are not allowed by hoa.