Key West Holiday Rentals, Florida: Private House Rentals

Our top choices for Key West hotels

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

New Town

Deetriss

฿6,177 total

includes taxes & fees

15 Jun - 16 Jun

Outdoor pool, pool umbrellas, pool loungers

Hampton Inn Key West FL

Key West

Lilia

฿6,148 total

includes taxes & fees

7 Jun - 8 Jun

Eden House

Key West Historic District

andrew

฿6,594 total

includes taxes & fees

15 Jun - 16 Jun

Courtyard by Marriott Key West Waterfront

Northside Resort

Kalena

฿6,214 total

includes taxes & fees

1 Jun - 2 Jun

Outdoor pool, open 6:00 AM to 10:00 PM, pool cabanas (surcharge)

Hilton Garden Inn Key West / The Keys Collection

New Town

RAFAEL G

฿5,422 total

includes taxes & fees

15 Jun - 16 Jun

2 outdoor pools, open 7:00 AM to 10:00 PM, pool cabanas (surcharge)

Blue Flamingo Resort Key West

New Town

Ania

฿6,770 total

includes taxes & fees

31 May - 1 Jun

Room, 2 Queen Beds, Balcony, Pool View | Balcony view

DoubleTree Resort by Hilton Grand Key - Key West

Key West

Stacey

฿7,010 total

includes taxes & fees

21 Jun - 22 Jun

Hyatt Vacation Club at Windward Pointe, Key West

Key West

Lisa

฿13,208 total

includes taxes & fees

27 Jun - 28 Jun

Authors of Key West Guest House

Key West Historic District

Royston

฿4,600 total

includes taxes & fees

31 May - 1 Jun

Ibis Bay Beach Resort

Northside Resort

Kim

฿9,143 total

includes taxes & fees

10 Jun - 11 Jun

Outdoor pool, open 7:00 AM to 10:00 PM, free pool cabanas, pool loungers

Fairfield Inn and Suites by Marriott Key West

New Town

Andrew

฿6,619 total

includes taxes & fees

21 Jun - 22 Jun

Southernmost House - Adult Exclusive

Old Town Key West

BOBBY J.

฿11,167 total

includes taxes & fees

21 Jun - 22 Jun

Silver Palms Inn & Historic Homes

Old Town Key West

Keith

฿6,925 total

includes taxes & fees

11 Jun - 12 Jun

The Marquesa Hotel

Old Town Key West

Julian

฿13,112 total

includes taxes & fees

31 May - 1 Jun

Cigar House King Suite w/ Poolside porch | Balcony view

Island City House Hotel

Key West Historic District

Michael

฿6,916 total

includes taxes & fees

24 Jun - 25 Jun

Westwinds Inn

Key West Historic District

michael

฿7,446 total

includes taxes & fees

28 May - 29 May

The Perry Hotel & Marina Key West

Stock Island

Sharon

฿7,474 total

includes taxes & fees

16 Jun - 17 Jun

The Palms Hotel

Old Town Key West

Eric

฿6,263 total

includes taxes & fees

2 Jun - 3 Jun

The Southernmost Inn - Adults Only

Old Town Key West

Patrick

฿6,031 total

includes taxes & fees

10 Jun - 11 Jun

Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Almond Tree Inn Hotel - Adults Only

Old Town Key West

Renee

฿8,855 total

includes taxes & fees

1 Jun - 2 Jun

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Holiday Rentals in Key West

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

"Courteous staff, very informative about local attractions"

Aparthotel

Island View 1BR Residence With Balcony

Key West

"Great place it is a full apartment with everything you could need and very clean "

Cottage

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Old Town Key West

"Property was clean and quiet nice amenities "

Cottage

Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

Beachside

"First timers and would definitely come back!! "

Cottage

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Old Town Key West

"The living room furniture and mattresses are not the most comfortable. Worn. Mattresses in small bedroom need replacement. Air conditioner does not reach small bedroom. "

Cottage

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

"Loved the closeness to Duval st and the privacy "

Cottage

Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

Stock Island

"Good detailed check in info and property info. Clean. Upstairs bath had standing water while showering. Bed downstairs very uncomfortable. Pool was nice but cold. "

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

Ocean Front 1BR Suite With Direct Beach Access

Key West

"Clean and spacious. Great view from room!"

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 Florida Keys Beaches are top sights worth seeing.

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Stay near popular Key West attractions

Duval Street

4.6/5 (20,928 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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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

Margaritaville Beach House Key West

4/10 Poor

"The hotel/resort was large yet the pool had 11 umbrella and many thirty loungers to use. It was almost impossible to get a seat in shade. The rooms had one chair in it that was extremely low to the floor and difficult to get in and out of. We did love the access to downtown shuttles. Next time I will stay somewhere else."

Southernmost Beach Resort and Guesthouses

6/10 Okay

"The property, itself was mostly clean. I expected Seagrass but was told nicer hotels with private beaches regularly clean up the seagrass. They did not! There were heaping mounds of stinky seagrass! I chose this resort for the use of their beach and it was unusable. The staff were nice, but seemed to not have appropriate information regarding the power outage. I was in the shower when it went out. It was out for a couple hours and I had to go to dinner with wet hair. When I came back to my room, the electric was back, but there was an incessant, loud buzzing/bell for about another half hour. The room, itself, was very clean and up to date. I didn’t use the pool as I wanted a beach experience. I ended up paying for an excursion to go to a sandbar."

Havana Cabana at Key West

10/10 Excellent

"This was such a fun hotel to stay in with an awesome pool and a shuttle to downtown so I didn't have to worry about finding parking. I especially loved the DJ at the pool every day spinning great tropical tunes combined with 80's dance music, and shots at 2PM daily! I wish I had stayed an extra night here because it was so much fun getting a suntan."

Blue Flamingo Resort Key West

6/10 Okay

"The property was clean and nice. They did leave my door unlocked and propped open when cleaning. Thank God nothing was taken. I did have an issue with how they handled the situation. They did offer 3 free drink tickets but I do not drink really. Used one and asked if they could maybe just comp the $16 dollar pizza I had ordered. They did not. Also, I had to email to have the drink removed because it was charged to me. Not a huge deal I just did not like that. It’s not a cheap resort to stay at. They could have handled the situation better in my opinion."

More cheap stays in Key West

Simonton Court Historic Inn & Cottages

320 Simonton St Key West FL

฿4,870

฿5,479 total

3 Jun - 4 Jun

includes taxes & fees

9.8/10 Exceptional! (964 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?

Blue Flamingo Resort Key West is a hotel with 2 outdoor pools and 2 restaurants, and it's a top choice on Expedia for families. Other good choices for your child-friendly holiday include Margaritaville Beach House Key West 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 Casa Marina Key West, Curio Collection by Hilton. 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 Casa Marina Key West, Curio Collection by Hilton and Ibis Bay Beach Resort. 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 free WiFi. 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?

Beachside Resort & Residences is a top hotel that has an adjacent golf course and features a marina. Another good option is Oceans Edge Key West Resort, Hotel & Marina 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 Ibis Bay Beach Resort and DoubleTree Resort by Hilton Grand Key - Key West. View all hotels with pools in Key West.

What is the best spa hotel in Key West?

Casa Marina Key West, Curio Collection by Hilton is a top spa hotel featuring a private beach, a fitness centre, a bar and a restaurant. Spend an afternoon at Spa Al Mare where you'll find facials, body scrubs, and deep-tissue massages and more. Other popular spa hotels in Key West include Southernmost Beach Resort and Guesthouses 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. Top sights in the city include Duval Street and Florida Keys Beaches. In Key West, there are 2685 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 Florida Keys National Marine Sanctuary are fun for children of all ages. Landmarks like Audubon House and Tropical Gardens, Mallory Square and Fort Zachary Taylor Historic State Park 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

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

Hampton Inn Key West FL

Eden House

Courtyard by Marriott Key West Waterfront

Hilton Garden Inn Key West / The Keys Collection

Blue Flamingo Resort Key West

DoubleTree Resort by Hilton Grand Key - Key West

Hyatt Vacation Club at Windward Pointe, Key West

Authors of Key West Guest House

Ibis Bay Beach Resort

Fairfield Inn and Suites by Marriott Key West

Southernmost House - Adult Exclusive

Silver Palms Inn & Historic Homes

The Marquesa Hotel

Island City House Hotel

Westwinds Inn

The Perry Hotel & Marina Key West

The Palms Hotel

The Southernmost Inn - Adults Only

Almond Tree Inn Hotel - Adults Only

Holiday Rentals in Key West

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

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

Learn more about Key West

Top Key West Hotel Reviews

Margaritaville Beach House Key West

More cheap stays in Key West

Simonton Court Historic Inn & Cottages

Frequently asked questions

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