Holiday rentals in Key West

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Top-rated holiday rentals in Key West

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Guest favourite

Bungalow in Key West

4.93 out of 5 average rating, 103 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

4–11 Dec

$795 SGD per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

4–11 Jul

$295 SGD per night

Superhost

Holiday 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.

21–28 Jan

$551 SGD per night

Guest favourite

Home in Key West

4.97 out of 5 average rating, 205 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

27 Aug – 3 Sep

$623 SGD per night

Guest favourite

Guest house 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.

23–30 Jun

$496 SGD per night

Guest favourite

Apartment in Key West

4.89 out of 5 average rating, 141 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).

16–23 Nov

$971 SGD per night

Guest favourite

Apartment 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.

25 Nov – 2 Dec

$831 SGD per night

Superhost

Flat in Key West

4.89 out of 5 average rating, 895 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.

19–26 Aug

$344 SGD 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.

10–17 Feb

$706 SGD per night

Guest favourite

Flat 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).

30 Mar – 6 Apr

$1,025 SGD per night

Guest favourite

Flat in Key West

4.93 out of 5 average rating, 15 reviews

Oceanfront Condo in Key West

Key West Beach Club is a serene waterfront oasis located in an upscale gated community within walking or biking distance to the local’s finest spots, including restaurants, beaches, shopping centers, bars and the infamous Duval Street. This complex prides itself for being one of the very few on the island that sits directly on the water.

24–31 May

$947 SGD per night

Guest favourite

Flat in Key West

4.94 out of 5 average rating, 358 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.

13–20 Aug

$351 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Key West holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Key West's top sights

Duval Street62 locals recommend

Mallory Square100 locals recommend

Key West Butterfly and Nature Conservatory56 locals recommend

Fort Zachary Taylor Historic State Park47 locals recommend

Higgs Beach21 locals recommend

Sebago Watersports6 locals recommend

Other great holiday rentals in Key West

Superhost

Home in Upper Sugarloaf Key

4.86 out of 5 average rating, 44 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

28 Jan – 4 Feb

$1,491 SGD per night

Superhost

Flat in Key West

5.0 out of 5 average rating, 4 reviews

Downtown KeyWest 2Bed Oceanfront

28 Jul – 4 Aug

$660 SGD per night

Guest favourite

Apartment in Key West

5.0 out of 5 average rating, 11 reviews

Spectacular Ocean View Amazing quality- Massage Ch

18–25 Jul

$1,032 SGD per night

Guest favourite

Apartment in Key West

4.99 out of 5 average rating, 78 reviews

*Come to my Deck for a time you won't Forget!

24–31 Oct

$614 SGD per night

Superhost

Apartment in Key West

4.85 out of 5 average rating, 39 reviews

Ocean front 1BR/1BA Suite w/ kitchen & living rm

4–11 Jan

$533 SGD per night

Guest favourite

Home in Key West

5.0 out of 5 average rating, 38 reviews

Gorgeous Romantic Private Villa, Steps from Duval!

2–9 Mar

$883 SGD per night

Superhost

Apartment in Key West

4.78 out of 5 average rating, 23 reviews

Casa Atlantica: A one bedroom condo on the

2–9 Sep

$557 SGD per night

Guest favourite

Apartment in Key West

4.92 out of 5 average rating, 13 reviews

1BR Condo - Pool View, Rooftop Balcony at Beachsid

15–22 Dec

$769 SGD per night

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Quick stats about holiday rentals in Key West

Total rentals	1.9K properties
Rentals with a pool	1.4K properties have a pool
Pet-friendly rentals	470 properties allow pets
Family-friendly rentals	1.2K properties are a good fit for families
Total number of reviews	54K reviews
Nightly prices starting at	$14 SGD before taxes and fees

Holiday rentals in Key West

Top-rated holiday rentals in Key West

Bungalow in Key West

Guest suite in Marathon

Holiday home in Key West

Home in Key West

Guest house in Key West

Apartment in Key West

Apartment in Key West

Flat in Key West

Houseboat in Key West

Flat in Key West

Flat in Key West

Flat in Key West

Holiday rentals for every style

Cabins

Flats

Houses

Popular amenities for Key West holiday rentals

Stay near Key West's top sights

Other great holiday rentals in Key West

Home in Upper Sugarloaf Key

Flat in Key West

Apartment in Key West

Apartment in Key West

Apartment in Key West

Home in Key West

Apartment in Key West

Apartment in Key West

Quick stats about holiday rentals in Key West

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

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