Vacation rentals in Fleming Key

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Top-rated vacation rentals in Fleming Key

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Guest favorite

Bungalow in Key West

4.93 out of 5 average rating, 104 reviews

Atlantis House's Banyan Suite-voted top 25 in USA

About this space Atlantis House with just two exclusive rooms, the Master suite and the Garden suite, is the most private and romantic guesthouse in Key West. Rated a 2021 Travelers’ Choice Award by Trip Advisor. Perfect for Honeymoons and Anniversaries. A "little jewel" tucked away inside a lush tropical garden just steps away from the beaches. NOTE: Superhost Shari is a new owner of this property. Past reviews do not transfer but are 5-STAR! This suite The Banyan Suite (previously called Garden Suite) is nestled in the corner of the lush backyard with a private French door entrance off the deck. This charming hideaway offers a large flat screen TV visible from the sofa and spacious king bed. Relax to island music on the Bose Mini Bluetooth speaker while you power up devices on provided chargers for countless photo op filled adventures that await! A corner bar table provides the perfect spot to enjoy a quick bite from the quaint kitchenette equipped with a mini-fridge, microwave oven, toaster, and coffeemaker, featuring famous Cuban coffee! Rejuvenate in the coveted in-room whirlpool bath with bubbles and soaking salts or cool off in the open shower with bench seating. The vanity is stocked with many toiletries and our white all-cotton bath robes allow for an extended spa experience. Please Note: The Banyan Suite is one of only two guest suites, separate from the Main Residence. The two suites have exclusive use of the lush backyard oasis with tropical trees, plenty of seating areas to enjoy the natural sounds of local wildlife or the pages of a good book. There is also a shared propane BBQ on the deck and an additional refrigerator with extra storage & ice located next to the complimentary cruiser bikes! The Banyan and Palm Suites each accommodate a maximum of 2 adults – Special accommodation for children may be included if the two guest suites are booked together. Guest access Guests have their own private entrance. Past reviews 5.0 out of 5 stars Cleanliness 5.0 Accuracy 5.0 Communication 5.0 Location 5.0 Check-in 5.0 Value 5.0

Feb 4 – 11

G$185,030 GYD per night

Guest favorite

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.

Jul 1 – 8

G$111,281 GYD per night

Guest favorite

Houseboat in Key West

5.0 out of 5 average rating, 21 reviews

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

Jan 1 – 8

G$86,449 GYD per night

Superhost

Vacation home in Key West

4.88 out of 5 average rating, 226 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.

Mar 6 – 13

G$84,600 GYD per night

Superhost

Houseboat in Key West

4.84 out of 5 average rating, 174 reviews

Happys Houseboat

This beautiful houseboat is nestled in a calm protected bay, it has hot water, a fridge and Air Conditioning! This boat was featured in Old Dominion‘s music video “I was on a boat that day”. Beautiful sites all around to wake up on the water and sunsets and stars to experiences as you relax on the top deck in the evening. Included in the rental is use of a skiff to get to and from land and and a seventh generation local captain to assist in check in and give a tour of the Houseboat.

Aug 4 – 11

G$79,802 GYD per night

Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 526 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

G$76,233 GYD per night

Guest favorite

Condo in Key West

4.88 out of 5 average rating, 144 reviews

Large waterfront 2/2 end unit with boat slip

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grills, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Sep 3 – 10

G$119,457 GYD per night

Guest favorite

Condo in Key West

4.96 out of 5 average rating, 76 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.

Nov 25 – Dec 2

G$127,653 GYD per night

Superhost

Apartment in Key West

4.89 out of 5 average rating, 904 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.

Aug 16 – 23

G$52,467 GYD per night

Superhost

Houseboat in Key West

4.92 out of 5 average rating, 39 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.

Feb 11 – 18

G$108,463 GYD per night

Guest favorite

Apartment in Key West

4.97 out of 5 average rating, 236 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).

Feb 8 – 15

G$167,065 GYD per night

Guest favorite

Apartment in Key West

4.94 out of 5 average rating, 359 reviews

Studio Blu - Key West, FL - Hip Studio in 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.

Jul 28 – Aug 4

G$57,104 GYD per night