Holiday rentals in Key West

4.98 out of 5 average rating, 505 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.

Apartment 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

Apartment in Key West

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!

4.95 out of 5 average rating, 319 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

This Historic unit has Pale blue interiors, small efficiency kitchen, platform Pottery Barn King memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bose Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!

Superhost

Holiday home in Key West

4.87 out of 5 average rating, 322 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.

Houseboat in Stock Island

4.96 out of 5 average rating, 23 reviews

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

Superhost

Boat in Marathon

4.79 out of 5 average rating, 272 reviews

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.

Superhost

4.88 out of 5 average rating, 1,504 reviews

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

Apartment in Key West

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.

4.89 out of 5 average rating, 352 reviews

Cottage in Key Largo

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals

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.

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

Flats

Convenient locations with everyday essentials

Popular amenities for Key West holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Key West

Home in Key West

5 out of 5 average rating, 4 reviews

Beautiful quiet neighborhood. Sunsets! Huge Pool!

DiegoRating, 5 stars9 months ago

I chose this house for our summer vacation with my family, and I have to say, it was absolutely spectacular. Upon arrival, you drive up to a stunning view of the pool and the beautiful water right in front of the house. Inside, the rooms are spacious with incredibly comfortable beds. The kitchen is a dream, and you can enjoy the sea view while cooking, relaxing in the living room, or from the balcony. The pool and yard quickly became our favorite spots, where we spent most of our time. The pool was always clean, with Samantha ensuring the maintenance team stopped by weekly. We also had access to a grill, which we used for amazing BBQs while watching the breathtaking sunsets that this home offers. The deck is another highlight, with two beautiful chairs perfect for relaxing with a book or chatting with loved ones. You can even park a jet ski or small boat right on the deck, which can be rented from local companies who will deliver it directly to the house. unforgettable vacation.

4.87 out of 5 average rating, 122 reviews

Private room in Key West

Alhambra

StevenRating, 5 stars1 week ago

We loved staying here. The garden was beautiful and the pool was perfect for my wife and I. Charles and Karen were very accommodating for us.

5 out of 5 average rating, 7 reviews

Apartment in Key West

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

ElizabethRating, 5 stars5 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.

4.98 out of 5 average rating, 44 reviews

Hotel room in Key West

Marrero's Guest Mansion Adult Only (21+) Room 12

JoseRating, 5 stars2 weeks ago

The rooms were fun and clean and quiet. We had a beautiful view of the pool and tropical landscaping.

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!

5 out of 5 average rating, 9 reviews

Duval Corner - Pet friendly with Balcony

ValerieRating, 5 stars5 days ago

We had a great time in Key West and love that we had the option to bring our pups while we stayed here! Was so happy to discover the sofa is a pull out sleeper. The host was able to accommodate a last minute change of plans, which we are so grateful for. There was always an open free parking spot on the street. The location was a short walk to everything you’d want to see! Thank you for a great stay and going above and beyond to accommodate us!

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.