Vacation rentals in Naval Air Station Key West, Monroe County

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Top-rated vacation rentals in Naval Air Station Key West, Monroe County

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Guest favorite

Home in Key West

4.95 out of 5 average rating, 343 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.

Top guest favorite

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.

Houseboat in Stock Island

4.96 out of 5 average rating, 26 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.

Superhost

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

4.8 out of 5 average rating, 274 reviews

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.

Superhost

A covered patio is visible with comfortable seating arrangements, featuring a wooden bench and lounge chair. The glass doors provide a view into the living area, with greenery visible from the surrounding environment. Light reflects off the water, adding to the peaceful ambiance.

Houseboat in Stock Island

5 out of 5 average rating, 4 reviews

Great Ocean Views! No regrets

Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. There is a little something for everyone from adventure seekers, to people who just want to get away and enjoy island life. You will see all kinds of sea life including a manatee from time to time! From deck view gorgeous sunsets, various sea birds catching their meals and even a military jet formation on occasion. Many great areas to kayak/paddle board off the boa.

Guest favorite

An inviting pathway is flanked by charming wooden structures, featuring pale green shutters. Lush greenery and tropical plants complement the brick walkway, leading toward the lush landscape beyond. The setting conveys a sense of tranquility and a connection to the vibrant surroundings.

Condo in Key West

4.88 out of 5 average rating, 241 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Top guest favorite

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.

Condo in Key West

4.97 out of 5 average rating, 101 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.

Guest favorite

A waterfront seating area is portrayed, featuring round tables surrounded by teal chairs. Umbrellas provide shade as guests enjoy the scenic view of the sunset over the water. The outdoor space is paved with light-colored bricks, enhancing the open and inviting atmosphere.

Boat in Key West

4.9 out of 5 average rating, 187 reviews

Stay on the Roxie!

Enjoy, peaceful, ocean-breezy, star-filled nights, on the water! Free parking and free round trip transport 1 to & 1 from Roxie per night’s stay! Roxie is anchored in a protected, shallow 3-4ft lagoon. We live on a boat a half-mile away should you need anything. 😊 Roxie has a Keurig, snacks like chips, breakfast muffins or donuts , Keurig pods, bread, peanut butter and jelly, and bottled waters. No cooking but you may bring to go food, drinks. 🛥️🌴

Superhost

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

4.88 out of 5 average rating, 248 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 serene outdoor area is highlighted by a clear blue salt-water pool surrounded by lounge chairs. Palms sway gently in the breeze, and a dining table sits nearby. The water view invites a sense of tranquility, complemented by landscaped greenery along the perimeter.

Townhouse in Key West

5 out of 5 average rating, 11 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.

Top guest favorite

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.

Condo in Key West

5 out of 5 average rating, 34 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.

Top guest favorite

A garden pathway is illuminated softly by evening light, flanked by charming garden beds. A bicycle is parked nearby, while a comfortable seating area invites relaxation. The pathway connects two buildings, showcasing the welcoming ambiance of the shared outdoor spaces.

Apartment in Key West

4.94 out of 5 average rating, 418 reviews

Studio Blu -Hip Studio/Old Town

Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this Studio apartment is minutes from everything on the island. No cars are necessary, bikes & beach chairs are provided free of charge.