Vacation rentals in Raccoon Key

4.91 out of 5 average rating, 285 reviews

A spacious porch is featured, surrounded by lush greenery. White railings border the space, while a dining set is positioned on the left. Natural light filters through the area, complemented by a ceiling fan overhead, enhancing the outdoor experience.

Townhouse in Key West

Comfortable, clean,beautiful home Summer Special

Introducing a brand new property hosted by AirBnb Superhost Roy Svenningsen. This home was fully renovated in January 2019. It features all new furnishings, stainless steel appliances, new flooring, marble countertops, and top quality mattresses. I look forward to hosting you in this beautiful family oriented gated community situated across from the Key West Golf Course and only 3 miles from Duval St. The home comes with parking for 2 cars. I am always available to answer any questions. Roy

4.95 out of 5 average rating, 319 reviews

A charming exterior features a bicycle adorned with vibrant flowers, positioned above a welcoming entrance. Lush greenery surrounds the quaint home, enhancing the tranquil atmosphere. The light blue siding and striped awning add to the inviting character of the property.

Apartment in Key West

Honeymoon Hideaway, King bed, Private Deck & Spa!

This Historic unit has Pale blue interiors, small efficiency kitchen, platform Pottery Barn King memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bose Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!

Houseboat in Stock Island

A clear swimming pool reflects the blue sky, surrounded by lounge chairs and umbrellas. Palm trees provide shade along the edge, complementing the vibrant greenery. In the background, modern multi-story buildings showcase balconies, offering a relaxed atmosphere by the water.

4.96 out of 5 average rating, 23 reviews

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

4.8 out of 5 average rating, 271 reviews

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

4.68 out of 5 average rating, 415 reviews

Apartment in Key West

Sunshine Suite Condo Enjoy outdoor Hot tub & Pool

Our Private condo 2 bedrooms & 2 bathrooms is for you to Enjoy your Vacation. Full equipped kitchen King sized beds in each room and 1 Queen-sized pull out sleeper sofa-bed in the living room. Family friendly Free WiFi Free parking !NO SMOKING in the apartment - on the balcony only with the closed balconies doors! NO SHOES IN THE HOUSE NO FOOD IN BED NO OIL/ OILY SKIN in BED NO Make-up wash off with our towels NO auto tan and etc wash off with our towels Late check out fee: $50/hour

4.97 out of 5 average rating, 100 reviews

A multi-level wooden structure is surrounded by tropical foliage and palm trees. Relaxing lounge chairs are positioned on the sandy beach, accompanied by umbrellas. Large, light-colored rocks frame the foreground, contrasting with the vibrant greens of the landscape and the serene blue sky above.

Condo in Key West

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.91 out of 5 average rating, 151 reviews

A spacious bar and grill area features wooden flooring and exposed beams, with multiple tables surrounded by green chairs. A long bar is positioned in the background, visibly stocked. Walls display various signs and decor, creating a relaxed dining atmosphere.

Townhouse in Key West

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat 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, kayaks, paddle boards and golf carts can be rented locally

4.89 out of 5 average rating, 142 reviews

The bathroom features a clean and modern design with a sink, mirrored cabinet, and a shower. A stacked washer and dryer unit is conveniently located near the entrance, providing accessible laundry facilities. Soft lighting enhances the neutral color palette throughout the space.

Condo in Key West

Tropical Escape at Sunrise

We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

4.87 out of 5 average rating, 246 reviews

Houseboat in Key West

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 ~

4.96 out of 5 average rating, 280 reviews

A charming entrance is revealed by a white picket fence, leading to a lush, landscaped pathway bordered by tropical greenery. A spacious patio area with dining furniture is visible under a large awning, while the upper balcony invites relaxation among the palm trees.

Apartment in Key West

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

Camper/RV in Stock Island

A well-equipped kitchen area features a modern sink set into a light-colored countertop. Near the sink, a red coffee maker, a black tap, and a white bottle are positioned, along with a white utensil holder. Natural light enters through a window, highlighting the space.

4.96 out of 5 average rating, 52 reviews

Rooster Camper at Leo's

Our lovely Rooster Camper is located in Stock Island and is the perfect place for your Key West getaway. Located only two blocks from the entrance to Key West, you can ride a bicycle, scooter, or golf cart to Key West from here. This place is located inside Leo's RV park and you can enjoy the amenities we have in place during your stay.

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Other great vacation rentals in Raccoon Key

4.95 out of 5 average rating, 20 reviews

Two wooden chairs provide seating on the deck of the houseboat, facing the open waters of Key West. Large glass doors lead into the kitchenette area, with a view of the serene sea and sky, emphasizing the peaceful outdoor setting.

Houseboat in Key West

Shanty Pineapple Key West

BlakeRating, 5 stars3 days ago

Tony was an excellent host! We are locals and did this as a staycation. Beautiful views, and really comfortable space. Highly recommend this spot! The kayak was an awesome addition, there’s a little sandbar and island close by. Would definitely do this again.

Home in Key West

4.79 out of 5 average rating, 52 reviews

Waterfront Home, Heated Pool - The Seagate Estate

AnneRating, 5 stars1 month ago

The house and pool were absolutely gorgeous! It was great. There was a bit of noise traffic and I wished we were a bit closer to Duval St., but it is a great place if you are with family and friends to hang out. I would definitely recommend it!!

A shared pool area is surrounded by lush tropical landscaping, featuring palm trees and greenery. Sun loungers and umbrellas are arranged around the pool, offering ample space for relaxation. The water reflects the clear blue sky, creating a serene and inviting scene.

Townhouse in Key West

4.87 out of 5 average rating, 141 reviews

Charming Key West Vacation Rental 3bedrm/3bath

PeterRating, 5 stars3 weeks ago

Great location, solid amenities, and the owner was very helpful in letting us stay late on our last day to let our kids have their rest time!! The only improvement I would suggest is to clean the floors as they were very dirty. But the pool was great, secure neighborhood, great little patios, and a well-stocked kitchen! Couldn’t really ask for more!

Several Aqualodges are positioned along a calm waterway, featuring white exteriors with metal roofs. Each lodge is adorned with outdoor seating arrangements of blue chairs, reflecting in the water beneath a clear blue sky.

Houseboat in Key West

4.74 out of 5 average rating, 190 reviews

Deluxe Bungalow

BradleyRating, 5 stars4 days ago

Aqua lodges were exactly as described and just what we needed. The value was great and we had a blast staying there. Marina restaurant was really good too.

A beachside gathering area includes six lounge chairs arranged around a circular fire pit, surrounded by white sand. Palms gently sway in the breeze, and a restaurant is visible in the background, contributing to a relaxed outdoor setting.

Boat in Key West

5 out of 5 average rating, 4 reviews

Luxurious 40' Sailing Yacht!

ChristianRating, 5 stars2 days ago

We spent four amazing days aboard the Shelly Kay with Blue Ocean Yacht Charters, and it was truly an unforgettable experience. From the moment we arrived, Cassey made sure we felt welcome and taken care of. She was incredibly attentive, quick to help with any questions or small issues, and always available when we needed her. The boat itself was in top shape—immaculate, well-maintained, and surprisingly spacious. Our quarters were very comfortable and had everything we needed to relax and enjoy the trip. It felt like our own private floating resort! Our excursion was the highlight of the stay—stunning views, smooth sailing, and such a peaceful way to explore the beauty of Key West. We couldn’t have asked for a better experience. If you’re looking for a unique and luxurious way to enjoy the Keys, this is it. We’ll definitely be back!

4.9 out of 5 average rating, 42 reviews

A welcoming entrance to the Truman Annex is framed by large, lush trees offering shade. The driveway leads toward a gate marked with a sign, while a pedestrian path runs alongside, inviting exploration of the surrounding area.

Condo in Key West

Walk to beach, Duval Street, Mallory Square

WendyRating, 5 stars2 weeks ago

Felt right at home from first step inside! Loved watching the iguana and geckos out back and the pool was a welcome cool down. Very close to all the action but peaceful and serene and safe feeling at the homestead! Perfect!!! Great hosts to answer local details on where to go! Fully enjoyed this Airbnb trip!