Vacation rentals in Cow Key Channel

A serene beach scene features gentle waves lapping against a sandy shore. Tall palm trees sway lightly in the breeze, and a rocky jetty extends into the calm waters, providing a tranquil view of the distant sea and sky.

4.95 out of 5 average rating, 151 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

4.91 out of 5 average rating, 285 reviews

A spacious porch is shown with a wooden deck and white railing. A ceiling fan is present above, offering a cooling feature. Nearby, a small table and chairs create a seating area surrounded by lush green vegetation, providing a private outdoor space for relaxation.

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

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.

4.95 out of 5 average rating, 319 reviews

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.

4.68 out of 5 average rating, 415 reviews

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

A wooden pier extends into calm waters, leading towards a beach with soft golden sand. In the background, a multi-story building is nestled among palm trees, set against a sky with scattered clouds and a single bird in flight.

4.97 out of 5 average rating, 100 reviews

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.

4.86 out of 5 average rating, 185 reviews

A waterfront bar and grill setting features a wooden deck lined with colorful adirondack chairs. Palm trees provide greenery and shade. The entrance reveals diners inside, enjoying the relaxed atmosphere, with boats docked nearby reflecting in the calm water.

Townhouse in Key West

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!

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.

4.89 out of 5 average rating, 142 reviews

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.

4.89 out of 5 average rating, 56 reviews

A spacious saltwater pool is surrounded by palm trees and lounge chairs, creating a relaxed atmosphere. Several umbrellas provide shade around the pool area, with vibrant red and blue accents visible. The clear water reflects the blue sky, inviting guests to enjoy a refreshing swim.

Houseboat in Key West

The simple life on Seaplicity!

Come stay on our beautiful & Super Comfy 38 ft Hunter Sailboat at the Perry Hotel & Marina! Start your morning with a fresh cup of coffee on board & "SIMPLIFY" your vacation with unrestricted access to all resort amenities! Two heated salt water pools, gym, laundry, and bathrooms and try one of the great restaurants onsite. Shuttle service takes you to old town Key West, leaving every hour from the hotel lobby.

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.

4.96 out of 5 average rating, 280 reviews

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).

A serene beach scene features a sailboat anchored near the shore, with gentle waves lapping at the sand. Palm trees sway in the breeze, while a clear blue sky provides a vibrant backdrop to the peaceful setting.

5 out of 5 average rating, 32 reviews

EYW Getaway

Relax with the whole family at this peaceful place to stay. Our two-bedroom two-bathroom condo with complete kitchen is located at Sunrise Suites Resort. Amenities include shared heated pool, hot tub, tennis court and a basic gym. Our condo is located 1mile from the airport, 1.5 miles from the beach and 3.5 miles from downtown Duval St.

4.87 out of 5 average rating, 246 reviews

A tranquil beachfront scene showcases a sandy shore lined with palm trees. Calm waters reflect the sky, dotted with fluffy clouds. In the distance, a marina displays boats alongside wooden docks, while cozy thatched-roof structures provide shaded seating.

Houseboat in Key West

Key West Luxury Houseboat at Yacht Club Resort

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

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Other great vacation rentals in Cow Key Channel

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 stars2 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.

4.86 out of 5 average rating, 22 reviews

A white wooden sign displays the words 'Garden House' surrounded by lush green foliage. Tropical plants and palm leaves frame the sign, creating a serene and inviting atmosphere in the outdoor setting.

Private room in Key West

Garden House Queen Room

RussRating, 5 stars3 weeks ago

Amazing stay and even better than expected. The room was quaint and everything we needed. Close enough to walk everywhere. The amenities were great. I had forgotten there’s a little pool and that was a great treat after a long day in the sun. We’re already looking to book again!

4.8 out of 5 average rating, 5 reviews

Coconut Mallory 2 BD Condo-218

CatharineRating, 5 stars4 months ago

A wonderful place for our family to enjoy Key West! The unit was exactly as described and very easy to access. Host was communicative leading up to and throughout our stay. Excellent value, and I would highly recommend!

A serene beach scene is captured at sunset, with gentle waves lapping at the shoreline. Palm trees sway softly beside blue lounge chairs on a pebbled beach, where tall grasses add texture. The sun sets on the horizon, creating a calming atmosphere over the water.

Condo in Stock Island

4.75 out of 5 average rating, 395 reviews

Private Parking & Waterfront - Grand Marina Suite

JRating, 5 stars1 month ago

Fantastic stay in a fantastic place! Highly recommended! Thank you very much

A spacious shared balcony is highlighted by a light blue ceiling and white railings. Several white chairs are arranged along the length, offering views of lush palm trees and rooftops of nearby structures. Natural light illuminates the area, enhancing the relaxing atmosphere.

5 out of 5 average rating, 7 reviews

Duval Corner - Pet friendly with Balcony

JulianRating, 5 stars3 weeks ago

Beautiful little apartment right on Duval Street. Really was a small slice of paradise.

4.88 out of 5 average rating, 355 reviews

A balcony is presented with several beige chairs arranged around a small table. A potted orchid adds a splash of color. The space features wooden flooring and is bordered by white railings and dark shutters, providing a cozy outdoor seating area.

Private room in Key West

Mallory House Room #1

AubreyRating, 5 stars2 weeks ago

My husband and I enjoyed our 3 night stay here! David was a wonderful host - very responsive, and even helped us check-in early. The room and common areas were kept very clean, and the location was very walkable. We would gladly stay here again!