Key West Holiday Rentals, Florida: Private House Rentals

Our top choices for Key West hotels

The Cabana Inn Key West - Adults Only

Old Town Key West

PATRICIA

฿7,580 total

includes taxes & fees

4 May - 5 May

Margaritaville Beach House Key West

Key West

jeronimo

฿10,876 total

includes taxes & fees

6 May - 7 May

Ocean View 3BR Condo with Rooftop Balcony | Balcony

Beachside Resort & Residences

Key West

igor

฿10,196 total

includes taxes & fees

20 Apr - 21 Apr

Havana Cabana at Key West

New Town

merlin dean

฿8,606 total

includes taxes & fees

10 May - 11 May

4 outdoor pools, pool umbrellas, pool loungers

Parrot Key Hotel & Villas

Northside Resort

Christina

฿9,783 total

includes taxes & fees

6 May - 7 May

The Palms Hotel

Old Town Key West

Dawn

฿8,792 total

includes taxes & fees

5 May - 6 May

Outdoor pool, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)

DoubleTree Resort by Hilton Grand Key - Key West

Key West

Anthony

฿9,357 total

includes taxes & fees

10 May - 11 May

Ibis Bay Beach Resort

Northside Resort

Lydia

฿8,810 total

includes taxes & fees

13 Apr - 14 Apr

NYAH Key West - Adults Only

Key West Historic District

James

฿7,158 total

includes taxes & fees

10 May - 11 May

Heron House Court - Adult Only

Key West Historic District

James

฿7,868 total

includes taxes & fees

15 Apr - 16 Apr

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

New Town

Ashish

฿8,009 total

includes taxes & fees

10 May - 11 May

Suite, 1 Bedroom, Ocean View (Spacious | King) | In-room safe, individually decorated, individually furnished, desk

The Laureate Key West

New Town

Roberta

฿9,020 total

includes taxes & fees

20 Apr - 21 Apr

Aqua Lodges at Hurricane Hole Marina

Stock Island

Jordan

฿11,513 total

includes taxes & fees

7 May - 8 May

6 outdoor pools, free pool cabanas, pool umbrellas

Oceans Edge Key West Resort, Hotel & Marina

Stock Island

Matthew

฿11,470 total

includes taxes & fees

4 May - 5 May

2 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)

Blue Flamingo Resort Key West

New Town

Armando

฿9,240 total

includes taxes & fees

10 May - 11 May

Southernmost House - Adult Exclusive

Old Town Key West

Dan

฿12,689 total

includes taxes & fees

23 Apr - 24 Apr

L'Habitation Guest House

Key West Historic District

Pat

฿8,868 total

includes taxes & fees

3 May - 4 May

Duval Inn

Old Town Key West

Kristin

฿10,578 total

includes taxes & fees

13 Apr - 14 Apr

Duval House

Old Town Key West

Victoria

฿10,034 total

includes taxes & fees

5 May - 6 May

The Reach Key West, Curio Collection by Hilton

Old Town Key West

Joseph

฿13,346 total

includes taxes & fees

4 May - 5 May

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Holiday Rentals in Key West

Apartment

The Grenada Suite Pool View Private Balcony

Key West

"A little dated, but clean and well located."

Cottage

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

Old Town Key West

"Staff were awesome. Loved the trees and foliage and privacy."

Condo

Coconut Mallory Resort And Marina By Kees Vacations

Key West

"We did not go to the pools. We went to the beach when we went in the water. Parking was good."

Aparthotel

Grand Marina Suite by Brightwild Waterfront

Stock Island

"Nice place "

Aparthotel

Ocean Front 1BR Suite With Direct Beach Access

Key West

"Clean and spacious. Great view from room!"

Holiday Home

Capmar House by Brightwild Huge Home Pool

Raccoon Key

"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"

Aparthotel

Two Bedroom Residence With Balcony

Key West

"The roosters crowing early morning was irritating "

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Where to stay in Key West

Find the best Key West areas for the activities you enjoy most. Learn more about Key West

Old Town Key West

Old Town Key West captures the essence of island history with its pastel Victorian "Conch Houses" and lively atmosphere. Stroll past Ernest Hemingway's home where six-toed cats roam freely. The charming district buzzes with activity from Duval Street to Mallory Square's famous sunset celebrations. Explore this walkable area to discover hidden treasures like the Truman Little White House and Key West Butterfly Conservatory. Live music spills from open-air bars while local galleries showcase island artists. Rent a bicycle to navigate the narrow streets or simply wander among the bougainvillea-draped fences.

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Key West Style Three Bay House is a common style on the Keys. Photo taken on Key West, Florida, USA

New Town

Key West's New Town area offers a refreshing glimpse into local island living. Here residential streets create a peaceful retreat from tourist crowds. Find budget-friendly hotels and everyday conveniences like shopping plazas and supermarkets. Smathers Beach is just a short drive away for sun seekers. The area's suburban character makes it perfect for travellers who want authentic experiences with practical amenities. Most locals choose New Town for its relaxed pace and affordable dining options.

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Key West Historic District

Step into a vibrant slice of history in Key West's Historic District. This charming area blends Victorian architecture with tropical flair along its narrow brick streets. The area boasts Hemingway's former home, the Truman Little White House, and sunset celebrations at Mallory Square. Duval Street forms the lively backbone of this walkable district. Visitors can explore art galleries by day and enjoy live music venues by night. Fort Zachary Taylor offers swimming and Civil War history just steps from the six-toed cats at the Hemingway House.

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Downtown Key West

Historic City centre Key West captivates with its colourful charm and rich maritime legacy. Stroll along iconic Duval Street where Victorian architecture meets lively bars and shops. Ernest Hemingway's former home welcomes visitors with its famous six-toed cats and literary history. Join the nightly Sunset Celebration at Mallory Square where street performers entertain against breathtaking Gulf views. The Historic Seaport offers boat tours and waterfront dining options. Most attractions sit within easy walking distance, making City centre Key West perfect for exploring on foot.

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Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Key West Butterfly and Nature Conservatory are top sights worth seeing.

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Stay near popular Key West attractions

Duval Street

4.6/5 (20,923 reviews)

Stroll the vibrant heart of Key West where historic architecture meets lively entertainment. Evening visits offer the full experience of Duval Street's renowned music scene and spirited local culture.

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Southernmost Point

4.4/5 (17,200 reviews)

This colourful buoy marks the continental United States' southernmost point, just 90 miles from Cuba. Arrive early to capture your photo at this iconic Key West landmark without the typical crowds.

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Learn more about Key West

Stroll Duval Street's colourful shops and bars before catching the sunset celebration at Mallory Square with local performers. Explore Hemingway's historic home where six-toed cats roam freely, then snorkel the vibrant coral reefs just offshore.

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Top Key West Hotel Reviews

The Perry Hotel & Marina Key West

10/10 Excellent

"The hotel exceeded our expectations in every way. View from our room was incredible, overlooking the marina. Loved lounging on the patio attached to room. Food at both on site restaurants was delicious. Would definitely recommend!"

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"The staff were all very friendly and helpful, and took time to answer questions and make sure we had what we needed. The room was smaller than what it looked like in the photos, but it was not small. There was plenty of room and the space was very clean. The breakfast, while good, was very much like your standard Hilton (Hampton Inn) buffet breakfast with servers getting your drinks for you. The pool was clean and refreshing. We loved the large selection of lounges around the pool as well as the number of palm trees. They provided just enough shade. The poolside bar was very convenient with good food choices. Prices for all food items were comparable with food all over the island. The shuttle to and from the airport was quick and easy. It showed up within minutes of us calling to say we were ready for pickup. The same can be said for our return trip to the airport. The shuttle to and from the beach was also quick and easy, but only runs every two (2) hours. Our only issue with the entire stay, and it wasn't a big one, was with the shuttle to and from downtown. The shuttles they use are on the smaller side and at almost every hour the crowd waiting for the shuttle was larger than could be accommodated. Fortunately, they had a second shuttle that they also ran which typically picked up those who couldn't fit on the first run, but this was not advertised and there was always the fear of being left downtown for another hour. Overall we had a wonderful stay!"

More cheap stays in Key West

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

฿7,065

฿8,810 total

13 Apr - 14 Apr

includes taxes & fees

8/10 Very Good! (2,189 reviews)

Frequently asked questions

What's the best place to stay in Key West?

Based on our traveller data, Blue Flamingo Resort Key West is one of the top choices for your stay. This hotel offers 2 outdoor pools and 2 restaurants. Other good options for your visit include Southernmost Beach Resort and Guesthouses and Margaritaville Beach House Key West. See all available top hotels, or vacation rentals in Key West.

If I need to cancel my hotel reservation in Key West, will I receive a refund?

Yes! You'll find that most hotel room reservations are refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Key West.

What's the best place to stay on a budget in Key West?

Based on reviews, Ibis Bay Beach Resort is a popular hotel for our travellers who want a more economical choice, and features free breakfast and free Wi-Fi. Other good options for your budget-friendly stay include Southwinds Motel and Seashell Motel. View all budget hotels in Key West.

What's the best family accommodation in Key West?

Margaritaville Beach House Key West is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families. Other good choices for your child-friendly holiday include Southernmost Beach Resort and Guesthouses and Casa Marina Key West, Curio Collection by Hilton. Also, attractions such as Mel Fisher Maritime Museum and Florida Keys Eco - Discovery Center are fun for children of all ages. Find more child-friendly accommodations in Key West.

What's the best LGBTQ-friendly accommodation in Key West?

Beachside Resort & Residences is a top LGBTQ-friendly hotel that features a marina and a private beach. Margaritaville Beach House Key West and Casa Marina Key West, Curio Collection by Hilton are two other good options for your holiday. See all available hotels listed as LGBTQ-friendly in Key West.

What's the best dog-friendly place to stay in Key West?

Blue Flamingo Resort Key West is a top hotel for people travelling with their pets, and offers 2 restaurants and free WiFi for its human guests. Two other good options for you and your pet include Margaritaville Beach House Key West and Havana Cabana at Key West. See more pet-friendly hotel accommodations in Key West.

What's the best accommodation option for a beach holiday in Key West?

Margaritaville Beach House Key West is a top beach hotel offering a 24-hour fitness centre and digital TV, located within a short 13-minute walk of Florida Keys Beaches . Other good options for your beach trip include Southernmost Beach Resort and Guesthouses and Parrot Key Hotel & Villas. See more stays near the beach in Key West.

What's the best high-end hotel in Key West?

Oceans Edge Key West Resort, Hotel & Marina is a luxury hotel with 6 outdoor pools and a marina, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Another upscale choice for your trip is The Porch on Frances Inn. Find more luxury hotels in Key West.

What's the best boutique accommodation in Key West?

Amsterdam's Curry Mansion Inn is a favourite guest house with our travellers looking for stylish accommodation, and features 29 guestrooms, a garden and a deli. Weatherstation Inn and Artist House Key West are two other options for a boutique stay. See all boutique hotels in Key West.

What's the best accommodation for a golf trip to Key West?

Oceans Edge Key West Resort, Hotel & Marina is a top hotel that has an adjacent golf course and features a marina. Another good option is Beachside Resort & Residences if you'd like to stay near a golf course while in town. You can tee off at Key West Golf Club during your trip. See more golf hotels in Key West.

What are some accommodation options with pools in Key West?

Blue Flamingo Resort Key West is a top hotel with 2 outdoor swimming pools, 2 restaurants and 2 pool bars. A couple of other options that offer an on-site pool include Southernmost Beach Resort and Guesthouses and Parrot Key Hotel & Villas. View all hotels with pools in Key West.

What is the best spa hotel in Key West?

Southernmost Beach Resort and Guesthouses is a top beach spa hotel featuring 3 pools, a fitness centre, a beach bar and a restaurant. Enjoy a facial, couples treatments or massage at Petite Spa. In-room massages are also available. Other popular spa hotels in Key West include Casa Marina Key West, Curio Collection by Hilton and The Reach Key West, Curio Collection by Hilton. See all spa hotels in Key West.

What is staying in Key West like?

Travellers to Key West give high marks for the lively bar scene, seaside and live music scene. This city also attracts tourists with its entertainment and festivals. A top sight in the city is Duval Street. In Key West, there are 2596 hotels and other accommodation options to choose from. Find out more about Key West.

What are the top places to visit in Key West?

Known for its live music and festivals, cultural venues include Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum and Harry S. Truman Little White House. Attractions such as Mel Fisher Maritime Museum, Florida Keys Eco - Discovery Center and Key West Shipwreck Museum are fun for children of all ages. Landmarks like Audubon House and Tropical Gardens, Key West Historic Seaport and Mallory Square might be worth a visit. Take a look at what more there is to see and do in Expedia's Key West guide.

What's the weather like in Key West?

The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 23°C. Average annual precipitation for Key West is 956 mm.

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Our top choices for Key West hotels

The Cabana Inn Key West - Adults Only

Margaritaville Beach House Key West

Beachside Resort & Residences

Havana Cabana at Key West

Parrot Key Hotel & Villas

The Palms Hotel

DoubleTree Resort by Hilton Grand Key - Key West

Ibis Bay Beach Resort

NYAH Key West - Adults Only

Heron House Court - Adult Only

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

The Laureate Key West

Aqua Lodges at Hurricane Hole Marina

Oceans Edge Key West Resort, Hotel & Marina

Blue Flamingo Resort Key West

Southernmost House - Adult Exclusive

L'Habitation Guest House

Duval Inn

Duval House

The Reach Key West, Curio Collection by Hilton

Holiday Rentals in Key West

The Grenada Suite Pool View Private Balcony

Where to stay in Key West

Old Town Key West

New Town

Key West Historic District

Downtown Key West

Uptown - Upper Duval

Stay near popular Key West attractions

Duval Street

Southernmost Point

Learn more about Key West

Top Key West Hotel Reviews

The Perry Hotel & Marina Key West

More cheap stays in Key West

Ibis Bay Beach Resort

Frequently asked questions

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