Holiday rentals in Key West

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Top-rated holiday rentals in Key West

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Key West

4.94 out of 5 average rating, 287 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.

Guest favourite

Rental unit in Key West

4.98 out of 5 average rating, 462 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Guest favourite

Townhouse in Key West

4.92 out of 5 average rating, 247 reviews

Sparklng clean, renovated, beautiful, and spacious

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

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 192 reviews

Casa Mariposa: Easy walk to Sombrero Beach

***SUMMER SALE*** Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated by Forbes the #1 Airbnb for couples south of Orlando for 2024 and a top 10 Airbnb in Florida. Step from your private suite to our 50' chilled lap pool surrounded with swaying palm trees and tropical foliage, large coral stone patio, and extensive tropical gardens. Avoid beach parking fees at beautiful Sombrero Beach with a short stroll from your suite at Casa Mariposa!

Guest favourite

Apartment in Key West

4.99 out of 5 average rating, 86 reviews

*2 Blocks to Duval, Large Deck, Parking, Beach*

🐓Your ideal Island Location awaits! Only 2 blocks from the Famous Duval St, you are close to Mallory Square & just outside the entrance to Ft. Zachary Taylor State Pak & Beach. Enjoy all of your upscale comforts of Home in your Gated community of Truman Annex/Shipyard with a designated parking spot and beautiful Pool only steps away. You can enjoy relaxing on the rear Deck in the shade or soaking up some sun (2 ceiling fans keep it cooler). Book your next Memorable Key West Vacation!

Superhost

Holiday home in Key West

4.88 out of 5 average rating, 249 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.

Guest favourite

Apartment in Duck Key

5 out of 5 average rating, 18 reviews

Oceanfront and Sunrise Views!

Your family will be close to everything when you stay at this centrally-located place. Enjoy your stay in the highly desirable island of Duck Key, a bike/walk friendly island. This condo is located right beside Angler & Ale, a popular Florida Keys Marina-side Restaurant that is only a walk away. You can even walk to the bridge for popular fishing areas nearby. Want to enjoy aquatic activities? Sole Watersports is right at your backyard, book a jets Ki rental, snorkeling or sunset tour!

Guest favourite

Boat in Islamorada

4.92 out of 5 average rating, 330 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Guest favourite

Boat in Stock Island

4.93 out of 5 average rating, 29 reviews

Spacious Trawler @ Luxury Marina

This is a new listing but we are experienced AirBNBers. Keeping the price low to get some initial 5 star reviews! Welcome aboard our cozy 37-foot trawler, nestled at the prestigious Perry Marina, and discover Coconut Row, one of the largest - and last of its kind - live-aboard communities in the U.S. PLEASE VIEW VIDEO BEFORE BOOKING: search "Caretta walk through" on Youtube Access to amenities include 2 swimming pools, dockside restaurants and bars, fitness center and more.

Guest favourite

Guest house in Key West

4.93 out of 5 average rating, 541 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.

Guest favourite

Apartment in Key West

4.88 out of 5 average rating, 149 reviews

Spacious Updated Waterfront Condo, 2/2 Pool, Dock

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

Superhost

Rental unit in Key West

4.9 out of 5 average rating, 1,051 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.