Holiday houses in Key West

4.98 out of 5 average rating, 504 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.

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.

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!

4.87 out of 5 average rating, 322 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.

4.8 out of 5 average rating, 271 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.

4.84 out of 5 average rating, 1,338 reviews

At Mine | Key West 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!

4.89 out of 5 average rating, 238 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

4.97 out of 5 average rating, 100 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.

4.87 out of 5 average rating, 201 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

4.87 out of 5 average rating, 246 reviews

Houseboat in Key West

Key West Luxury Houseboat at Yacht Club Resort

PANORAMIC Ocean Views - POOL 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, 500 square foot Rooftop Sky-Deck - 2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV, 42 inch TV, 32 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

4.96 out of 5 average rating, 280 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).

4.94 out of 5 average rating, 415 reviews

Studio Blu -Hip Studio/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 free of charge.

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Key West holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Key West

4.95 out of 5 average rating, 20 reviews

Houseboat in Key West

Shanty Pineapple Key West

BlakeRating, 5 stars2 days ago

Tony was an excellent host! We are locals and did this as a staycation. Beautiful views, and really comfortable space. Highly recommend this spot! The kayak was an awesome addition, there’s a little sandbar and island close by. Would definitely do this again.

4.82 out of 5 average rating, 67 reviews

Blue Room at the Grand Maloney

DiegoRating, 5 stars2 weeks ago

Phenomenal place, the location was a big plus! you can walk everywhere. looking forward to staying again

4.71 out of 5 average rating, 173 reviews

Houseboat in Key West

A slice of paradise in the Florida Keys

CarmenRating, 5 stars3 months ago

Wonderful night! Only a few bugs around dusk that left by nightfall. Lots of planes took off from 5-7 PM, but again they stopped by nighttime and not sure that it happens every day. The boat itself was perfect, exactly as described!

Campervan/RV in Big Pine Key

5 out of 5 average rating, 28 reviews

Beautiful Private Camper Nature

TomasRating, 5 stars1 week ago

My stay in this Airbnb was perfect for my trip! The surrounding nature is beautiful— it’s right by Bahia Honda State Park, and the location of the Airbnb makes for seeing a lot of wildlife! Stephen was very kind and helpful and made sure I had a great stay. He was very flexible with check-in and check-out, and made sure the RV was super clean and comfortable.

5 out of 5 average rating, 11 reviews

Heron Hideaway

AllisonRating, 5 stars3 days ago

Great place to stay while in Key West far enough from Duval to be quiet yet close enough to walk to wherever you want to go. Very responsive host. The accommodations were just as pictured and described. I would recommend this place.

5 out of 5 average rating, 32 reviews

EYW Getaway

JesseniaRating, 5 stars1 week ago

We had a great stay! The place was clean, comfortable, and had everything we needed. The location was perfect, and communication with the host was smooth and easy. Would definitely stay here again, highly recommended!

5 out of 5 average rating, 18 reviews

Home in Key Colony Beach

Bohemian Beach Bungalow

AnnaRating, 5 stars1 week ago

I can’t say enough great things about this beach bungalow! From the moment we arrived, we were welcomed with warm hospitality and thoughtful touches that made our stay truly special. The bungalow itself is cozy, clean, and beautifully decorated with a laid-back coastal vibe—exactly what you want for a beach getaway. Whether you’re looking for a romantic escape, a solo retreat, or a peaceful base for beach adventures, this place is a gem. We left feeling refreshed and recharged, and we’re already dreaming of coming back!