Holiday houses in Key West

4.81 out of 5 average rating, 322 reviews

Houseboat in Key West

Key West Houseboat Paradise

5 Years SuperHost Rated with over 300 reviews!! ~ Single Stateroom with Queen Bed, ideal for a couple. Sleeps 1-4. Spacious living room, big sofas. Full kitchen, Full Bath, large Rooftop Sun Deck, 15 min to Duval St. The land-side isn't fancy. Light industrial, Old-school Key West feel. Blue collar, friendly working class, wooden dock with a working auto garage & warehouse but the water view of dozens of green mangrove island with 2 Sea Kayaks waiting for you to take exploring is a Hidden Gem.

4.95 out of 5 average rating, 342 reviews

Home in Key West

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.

Condo in Key Colony Beach

4.91 out of 5 average rating, 182 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

4.93 out of 5 average rating, 111 reviews

WALK TO BEACH, MALLORY SQUARE, DUVAL STREET

Key West a little piece of the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street. You're just a walk away from Zachary Taylor Park (where you can do yoga on the beach, swim, snorkel, or hang hammocks between the palms). We’re near numerous shops, restaurants, and museums. Enjoy coffee in the morning, wine at night on our oversized deck. THE ADJACENT UNIT MAY BE AVAILABLE FOR ADDITIONAL SPACE.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 109 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

4.87 out of 5 average rating, 323 reviews

Holiday home in Key West

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.

4.79 out of 5 average rating, 272 reviews

Boat in Marathon

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.

4.88 out of 5 average rating, 1,504 reviews

Apartment in Key West

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. Located on a quiet street, it offers a private pool and peaceful stay for vacationers and business travelers. The unit includes a comfy Queen bed, mini fridge, microwave, iron & board, hangers, TV, and AC. Enjoy Key West's warm weather year-round. This special place is close to everything, making it easy to plan your trip. Just a heads-up: Key West’s famous roosters love to strut and crow—part of the island charm!

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.

4.94 out of 5 average rating, 118 reviews

Home in Key Colony Beach

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

4.85 out of 5 average rating, 238 reviews

Apartment in Key West

Studio Near Downtown - The Bartlum

Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, located on Caroline St, has been designed with comfort in mind, offering large windows for natural sunlight and plenty of space to spread out. Enjoy an updated kitchen, spacious bathroom, open concept layout, and all the hot spots of Key west within walking distance!

4.96 out of 5 average rating, 280 reviews

Apartment in Key West

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).

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Key West holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Key West

5 out of 5 average rating, 7 reviews

Parking, Deck, Pool, Beach, 2 Blocks to Duval St

ElizabethRating, 5 stars6 days ago

Talk about location! You are in the heart of everything without the hassle of crowds. I would recommend bringing a bike or renting a moped bc the heat can make it a little tough to walk every day. Just find a spot with some shade and a nice breeze (Fort Zach beach is a great place to sleep off a handover), and you’re set for your vacation. Condo was clean and the kitchen was a nice perk for snacks in between eating.

Private room in Big Pine Key

4.97 out of 5 average rating, 36 reviews

Sweet Spot - Kayak and SUP launch

JuleeRating, 5 stars1 month ago

We had a wonderful time. I took my daughter down to the Keys because well she’s 17 and growing up too fast so we got some us time. Our love for the ocean is deep. Staying here was perfect to get to Key West to do some adventures and was so peaceful to hangout and chill. Once you walk into the Airbnb it smelled so good and was very clean. Our room and bathroom was perfect. The Big Pine Rooster was our favorite place to eat. The breakfast and dinner was amazing and my daughter said they had great key Lime pie. We used the kayaks and just wished we would have been able to go out into the ocean instead of having to stay in the “slipway area” would have been amazing. Lili the owners sister was there and was great. She made sure the house always smelled great and made sure we were doing good and comfortable. She gave us a couple free passes for put out golf and unfortunately we couldn’t use them. Overall it was such a great stay and would recommend to everyone!

Home in Marathon

5 out of 5 average rating, 4 reviews

The Roseate House at Grassy Key

MollyRating, 5 stars3 weeks ago

I don’t even know where to begin. From start to finish, our stay was absolute perfection. The views could not be beat. There are kayaks to venture out into the gulf and the mangroves, a pool that’s COOLED (you know how hot pools can get during the summer. It was so refreshing) and a garden oasis full of some of the most beautiful foliage I’ve ever seen. I’m from Charleston, SC. I’m used to waterfront living, but this was just something more magical than I could’ve ever predicted. I’m already planning my trip back for next year. Heidi left a great list of recs for restaurants and activities to do, but the property was so incredible, I only left to eat really. If you’re looking for a relaxing place to stay, with on site water days this is the place for you. The house is nice, but also has that old school beach vibe which is my absolute favorite. I just can’t say enough good things. Thank you so much, Heidi, for sharing your stunning home with us.

4.88 out of 5 average rating, 356 reviews

Private room in Key West

Mallory House Room #1

AubreyRating, 5 stars3 weeks ago

My husband and I enjoyed our 3 night stay here! David was a wonderful host - very responsive, and even helped us check-in early. The room and common areas were kept very clean, and the location was very walkable. We would gladly stay here again!

4.95 out of 5 average rating, 21 reviews

Hotel room in Key West

Marrero's Guest Mansion Adult Only (21+) Room 6

LeannRating, 5 stars3 weeks ago

Stop looking and book this place! You will NOT be disappointed. You will experience friendly staff, comfy beds, roomy and the pool was amazing and private. Absolutely great location! One block from Duval street!

4.77 out of 5 average rating, 61 reviews

Historical 2BR with pool, walk to Beach & Duval St

GloriaRating, 5 stars1 month ago

Thank you for everything. Beautiful place, very clean and close to everything.