Key West Hotels with a Pool

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Tonight
16 Apr - 17 Apr
Tomorrow
17 Apr - 18 Apr
This weekend
17 Apr - 19 Apr
Next weekend
24 Apr - 26 Apr

Key West Hotels with a Pool

Outdoor pool, pool umbrellas, pool loungers

Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
Key West
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • On private beach
  • Hot tub
8.6 out of 10, Excellent, (2,145 reviews)
Sparkling waters beckon at the marina-side pool complex, featuring loungers, umbrellas, and attentive poolside service. Kayaking adventures, white sand beaches, and a relaxing spa pool create perfect holiday days with stunning sunset views.
The price is AU$412
includes taxes & fees
20 Apr - 21 Apr
Beachside Resort & Residences
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Discover your perfect hotel with a pool in Key West

Breakfast included
Spa pool

Hotels with pools and free breakfast in Key West

Outdoor pool, pool umbrellas, pool loungers
Hampton Inn Key West FL

Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
Key West
9.0 out of 10, Wonderful, (1328)
The price is AU$453
includes taxes & fees
3 May - 4 May
Hampton Inn Key West FL
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Hotels with pools and spa pools in Key West

Property grounds
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1019)
The price is AU$669
includes taxes & fees
11 May - 12 May
Hyatt Vacation Club at Beach House, Key West
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4-star hotels with pools in Key West

Studio Suite | Terrace/patio
Eden House

Eden House

Eden House
4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1002)
The price is AU$391
includes taxes & fees
10 May - 11 May
Eden House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top neighbourhoods in Key West

Old Town Key West

Old Town Key West mixes Caribbean charm with historical treasures on every corner. Stroll past colourful Victorian "Conch Houses" with gingerbread trim to discover Ernest Hemingway's six-toed cats or the gleaming Truman Little White House. Duval Street buzzes with lively bars and music venues while Mallory Square hosts unforgettable sunset celebrations with fire jugglers and street performers. The area serves up everything from fresh grouper and conch fritters to key lime pie at spots ranging from waterfront fine dining to casual shacks. Most travellers explore the charming brick streets on foot or by renting bikes, with trolleys looping frequently through the walkable historic grid.

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

New Town

New Town gives you a quieter slice of Key West living away from the tourist crowds. This peaceful residential area offers wide streets for strolling and a glimpse into authentic island life. Nearby Smathers Beach and the Key West Tropical Forest provide natural escapes when you need a break from the bustle. Budget-friendly chain hotels and holiday rentals make this area wallet-friendly for longer stays. Cuban-American eateries and family restaurants offer affordable meals, while shopping plazas with supermarkets help you feel right at home. A car is handy, but free parking is plentiful throughout the area.

Key West Historic District

The Key West Historic District lets your inner wanderer loose on pastel-painted streets steeped in salty charm. Ernest Hemingway's old stomping grounds mix with lively bars and the nightly sunset celebration at Mallory Square. History buffs explore the Truman Little White House while party people hit Duval Street for live music and tropical drinks. Fresh seafood and Cuban-influenced cuisine fuel your adventures between historic Victorian B&Bs and boutique inns with tropical courtyards. Getting around is easy—just stroll the narrow brick streets, hop on a narrated trolley tour, or rent a bike to cruise this flat, compact island paradise.

Downtown Key West

City centre Key West dazzles with its historic charm and direct energy. Wander Duval Street's lively scene, visit Hemingway's famous six-toed cat sanctuary, or catch the sunset celebration at Mallory Square where fire-breathers and musicians perform against stunning Gulf backdrops. The neighborhood's Victorian mansions with gingerbread trim and weathered coral stone churches create a unique tropical atmosphere. The area serves up fresh seafood from casual waterfront joints to upscale restaurants. Most attractions sit within a walkable six-block radius, though you can hop on the Conch Tour Train when your feet need a break. Boutique hotels and historic inns with tropical courtyards offer charming places to crash after experiencing the legendary bar scene.

Uptown - Upper Duval

Key West's Uptown - Upper Duval neighbourhood has lots of places to visit, such as Duval Street and Florida Keys Beaches.

Top landmarks in Key West

Duval Street
Duval Street

Duval Street

5/5(5 reviews)

If you want to give your credit card some exercise, head out to Duval Street, a popular place for shoppers in Key West Historic District. Splash some more cash at We Cycle Key West and Mallory Dock.

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Mallory Square
Mallory Square

Mallory Square

4/5(3 reviews)

Mallory Square is worth passing through for a few pics when in Key West Historic District. Why not take a stroll along the beaches and watch the sunset while you're here?

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Frequently asked questions

What are the best hotels with a pool in Key West?
Based on guest reviews, Almond Tree Inn Hotel - Adults Only is one of the best Key West hotels with a pool. An electric car charging station and designer toiletries are included in your stay too. H2O Suites - Adults Only is another visitor favourite where you can lounge poolside. To find other highly rated options with this perk, simply use the "Pool" filter and then sort by "Guest rating + our picks."
What are the cheapest hotels with a pool in Key West?
It's easy to find some of the cheapest hotels in Key West with a pool from AU$287 for your next adventure. One of the most budget-friendly is Travellers Palm. It also offers a barbecue grill and a terrace. Weatherstation Inn is another place that delivers poolside fun on a budget.
What is the best time to stay in a hotel with a pool in Key West?
If you'd like to explore when it's less busy, book your stay for September. You could score some great deals on Key West hotels with a pool around then. The warmest weather is in July, with temperatures ranging from 28ºC to 29ºC. It's coolest in January, which has averages of between 20ºC and 22ºC.
What hotels with a pool are closest to Duval Street?
See the sights and then lounge by the water at Almond Tree Inn Hotel - Adults Only. Featuring an electric car charging station and pillow top mattresses, this property is a short drive from Duval Street. H2O Suites - Adults Only is another nearby option. Browse the variety of hotels in Key West with a pool that'll put you close to this popular attraction.
What hotels with a pool are closest to Key West Intl. Airport (EYW)?
Go from the hustle and bustle of the terminal to paddling around in the pool at Hyatt Holiday Club at Windward Pointe, Key West. It's around 2 kilometres east of Key West Intl. Airport (EYW). Additionally, you can make use of a jetted bathtub and a barbecue grill here. Hampton Inn Key West FL is another nearby option. Whether you're staying a while or on a layover, find a Key West hotel with a pool close to the airport and experience convenience and relaxation.
Are there any hotels with a pool in Key West with parking?
You'll find 2,671 Key West hotels with a pool and parking. Pull in and go for a dip at Almond Tree Inn Hotel - Adults Only. An electric car charging station and pillow top mattresses are included in your stay too. Or, head to The Marquesa Hotel, where you can easily access both parking and a pool.

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