Vacation rentals in Naval Air Station Key West

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Top-rated vacation rentals in Naval Air Station Key West

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Guest favourite

Home in Key West

4.94 out of 5 average rating, 270 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.

Sep. 21 – 28

$788 CAD per night

Superhost

Tiny homes in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

Oct. 13 – 20

$176 CAD per night

Guest favourite

Townhouse in Key West

4.87 out of 5 average rating, 174 reviews

*Sparkling new kitchen* 3 bedroom/3 bath home.

Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and two queen beds. The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer installed. The salt water pool is perfect for lazing away your days. There is on street parking for two cars. The center of town is ten minutes away. An entire home for the price of one hotel room.

Sep. 18 – 25

$728 CAD per night

Superhost

Houseboat in Key West

4.81 out of 5 average rating, 252 reviews

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

Jul. 25 – Aug. 1

$550 CAD per night

Guest favourite

Guesthouse in Key West

4.93 out of 5 average rating, 525 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Jun. 23 – 30

$546 CAD per night

Superhost

Apartment in Key West

4.89 out of 5 average rating, 897 reviews

At Mine | Key West Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Sep. 13 – 20

$435 CAD per night

Guest favourite

Condo in Key West

5.0 out of 5 average rating, 24 reviews

Gorgeous Ocean View in Paradise

This is paradise! Wake up to a gentle breeze and birds singing just outside your condo. 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: Yellowfin Bar & Kitchen on premises. Elevator Broken.

Aug. 20 – 27

$737 CAD per night

Guest favourite

Condo in Key West

4.92 out of 5 average rating, 13 reviews

1BR Condo - Pool View, Rooftop Balcony at Beachsid

Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in the perfect blend of adventure and relaxation in sunny Key West. On property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise. Don’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.

Nov. 28 – Dec. 5

$699 CAD per night

Superhost

Houseboat in Key West

4.92 out of 5 average rating, 38 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

Romantic getaway on the sea with panoramic views of the ocean. Capture each sunrise and sunset on board this one-of-a-kind, floating vacation suite. Luxurious amenities include a full en suite bath with a rainfall shower head, heated water, A/C, kitchenette, electricity, wi-fi, and even a projector in case you want to "Netflix & chill." Snorkel gear, kayak, and magic included.

Sep. 8 – 15

$763 CAD per night

Guest favourite

Townhouse in Key West

5.0 out of 5 average rating, 5 reviews

The Blue Water Oasis

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.

Aug. 13 – 20

$729 CAD per night

Guest favourite

Apartment in Key West

4.97 out of 5 average rating, 235 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).

Mar. 10 – 17

$1,217 CAD per night

Guest favourite

Home in Key West

4.98 out of 5 average rating, 41 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.

Sep. 9 – 16

$654 CAD per night