The Best Key West Hotels with Pools from $165 - Hotels with indoor pools in Key West, FL

Q: What are some hotels with pools in Key West?

Southernmost Beach Resort and Guesthouses : Hotel steps from South Beach. Features 2 pool bars, 3 outdoor pools, and a full-service spa. Parrot Key Hotel & Villas : Hotel located near Duval Street. Offers complimentary wireless internet access, 4 outdoor pools, and flat-screen televisions. The Perry Hotel & Marina Key West : Hotel located near Smathers Beach. Provides 2 restaurants, 2 outdoor pools, and 2 pool bars. Hilton Garden Inn Key West / The Keys Collection : Hotel located near Smathers Beach. Features 2 restaurants, a pool, and complimentary wired internet access. The Reach Key West, Curio Collection by Hilton : Resort steps from South Beach. Offers a private beach, an outdoor pool, and a full-service spa.

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Compare Key West Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

3 outdoor pools, pool umbrellas, sun loungers

"Great stay"

includes taxes & fees

$348 per night

May 27 - May 28

Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers

"Nice spot to stay and very affordable "

includes taxes & fees

$220 per night

May 6 - May 7

Outdoor pool, pool umbrellas, sun loungers

"Great place to stay!"

includes taxes & fees

$229 per night

Jun 1 - Jun 2

"Nice Hotel and clean with a large pool, close to the old town and shopping area and restaurants."

includes taxes & fees

$203 per night

Jun 1 - Jun 2

"Loved the sandy beach area, hammocks, and pier to watch the sunsets in the evening!"

includes taxes & fees

$223 per night

May 19 - May 20

"Very convenient location, walking distance to most attractions. Free parking, which is a very nice feature given its location."

includes taxes & fees

$210 per night

Jun 1 - Jun 2

Outdoor pool, open 7:00 AM to 11 PM, pool umbrellas, sun loungers

"The staff is what makes this property such a wonderful experience! No matter the individual staff members function, they are all focused on excellent guest experience! Special shout out to Constanta for making sure all our needs were met whether we were lounging at the pool or on the patio dining area or dining inside! She greeted us daily and made sure we were always being taken care of!"

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

"Staff is professional and pool is very nice."

includes taxes & fees

$208 per night

Jun 1 - Jun 2

Find out more about Key West

Booking hotels with pools in Key West on Expedia

Your dream vacation is just a few clicks away thanks to Expedia's amazing selection of hotels with pools in Key West. Finding them is as easy as lazing on a lounge chair thanks to the easy-to-use search wizard. All you need to do is select your dates and it'll return hundreds of fantastic options. With so many options to choose from, the filters come in handy as they let you tailor your search results based on your preferences.

If it's luxury you're seeking, select the “5-star” filter. From infinity pools that seem to blend into the horizon to swim-up bars where you can sip on margaritas in the water, this filter will show you the most opulent accommodations available. The “guest rating” filter will help you pin down Expedia's top-rated Key West hotels with a pool based on hundreds of reviews from fellow travelers. Once you've found your dream property, click through to choose your room and book. The detailed hotel descriptions on Expedia, including things like room size, cancellation policy, and info about the all-important swimming pool, means you'll know exactly what to expect when you arrive.

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Most booked related stays in Key West in 2025

Kid-friendly Key West hotels with a pool

Get ready to blow up the inflatable pool floats and swimming tubes, as you'll find a multitude of kid-friendly Key West hotels with a pool on Expedia. Select the “family-friendly” search filter to scan these. From splashing with mom and dad to playing around on pool noodles, your kids will love nothing more than long, sunny days in the water. Many family-friendly hotels boast children's pools with shallow water and dedicated lifeguards too, so you can rest assured your little ones are safe while playing.

Some hotels with pools also offer kids' clubs with fun activities and events to keep your youngsters entertained all day long. They'll be able to make new friends, learn how to swim, and play classic games like water volleyball and pool tag. Best of all, with your kids kept entertained, you'll be able to enjoy some well-earned “me time”. It's worth looking for all-inclusive plans, too. These make for a hassle-free family vacation as they include all meals and drinks, so you won't have to worry about eating out or cooking. Many family-friendly hotels even offer children's menus with your kids' favorite foods.

Key West spa hotels with pools

Click both the “pool” and “spa” filters on Expedia to view some of the best Key West spa hotels with pools. Picture yourself receiving a full body massage, easing the knots out of your back before diving into the refreshing water. The dreamy combination of therapeutic swimming and holistic spa treatments means you'll come back from vacation relaxed and glowing. Many hotels even offer hot tubs and wellness activities, like poolside yoga and meditation.

Plan your pool hotel stay in Key West

When looking for Key West hotels with swimming pools in 2025, it's worth researching which area you'd like to stay in. You can choose to be close to key attractions or in more distant places for something more secluded. Wherever you opt for, the “popular locations” and “neighborhood” filters make it a breeze to find hotels with pools in Key West's most popular areas. There are more than just hotels, too. Take advantage of the “property type” filter to view vacation homes with pools in Key West, including villas, condos, and private homes.

Recent reviews of Key West hotels

Hilton Garden Inn Key West / The Keys Collection

5/5 Excellent

"Great rooms. Clean, extra large, cool and quiet. Pool area is excellent, plenty of chairs. Lobby was welcoming and staff exceptionally helpful! Nice gym with plenty of equipment for a good workout. An excellent hotel in the Keys! Highly recommend. "

A verified traveler stayed at Hilton Garden Inn Key West / The Keys Collection

Posted 6 hours ago

The Gates Hotel Key West Newly Renovated

5/5 Excellent

Pet friend GATES

"I am truly grateful for hotels like this one where they allow your pets to stay. It’s convenient. It’s easy. Everyone was super friendly and really nice and accommodating. I’ve stayed there before and I’ll stay there again. Thank you !"

A verified traveler stayed at The Gates Hotel Key West Newly Renovated

Posted 2 days ago

Oceans Edge Key West Resort, Hotel & Marina

5/5 Excellent

"Great location for a quiet getaway. The resort has plenty of amenities, including restaurant and bar, 6 pools, and a gym. The rooms are clean, spacious, and thoughtfully designed, some including a terrace. There is also complimentary shuttle to Key West, 2hr bike and kayak rental. The only remark is that the rooms smell like cigarettes although staff has assured us the hotel has always been a smoke free. "

A verified traveler stayed at Oceans Edge Key West Resort, Hotel & Marina

Posted 3 days ago

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Frequently asked questions

What's it like visiting Key West?

If taking it easy by the pool is your idea of a great getaway, you might want to think about Key West, which has 117 places to stay with pools. While you’re here, you can explore attractions like Duval Street, and then relax and unwind poolside at one of the accommodations in Key West that travelers like for their pools.

What are some hotels with pools in Key West?

Southernmost Beach Resort and Guesthouses: Hotel steps from South Beach. Features 2 pool bars, 3 outdoor pools, and a full-service spa. Parrot Key Hotel & Villas: Hotel located near Duval Street. Offers complimentary wireless internet access, 4 outdoor pools, and flat-screen televisions. The Perry Hotel & Marina Key West: Hotel located near Smathers Beach. Provides 2 restaurants, 2 outdoor pools, and 2 pool bars. Hilton Garden Inn Key West / The Keys Collection: Hotel located near Smathers Beach. Features 2 restaurants, a pool, and complimentary wired internet access. The Reach Key West, Curio Collection by Hilton: Resort steps from South Beach. Offers a private beach, an outdoor pool, and a full-service spa.

How many hotels with pools are there in Key West?

Expedia’s 117 hotels in Key West give you a great choice for your poolside getaway.

What is there to see and do in Key West?

Explore places like Duval Street while you’re in Key West. The picturesque setting of Audubon House and Tropical Gardens and Key West Butterfly and Nature Conservatory showcase the area’s natural beauty. Key West appeals to visitors with its beautiful ocean views, great live music scene, and bar scene.

When is the best time to book a hotel with a pool in Key West?

Taking into account the local weather in Key West is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. Average annual precipitation for Key West is 38 inches.

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Compare Key West Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Southernmost Beach Resort and Guesthouses

24 North Hotel Key West - Newly Renovated

Hampton Inn Key West FL

The Gates Hotel Key West Newly Renovated

Parrot Key Hotel & Villas

Silver Palms Inn

Margaritaville Beach House Key West

Fairfield Inn and Suites by Marriott Key West

The Southernmost Inn - Adults Only

Oceans Edge Key West Resort, Hotel & Marina

Find out more about Key West

Booking hotels with pools in Key West on Expedia

Expand your search

Most booked related stays in Key West in 2025

Kid-friendly hotels

Vacation homes with pools

Spa hotels

Hotels with hot tubs

Kid-friendly Key West hotels with a pool

Key West spa hotels with pools

Plan your pool hotel stay in Key West

Recent reviews of Key West hotels

Hilton Garden Inn Key West / The Keys Collection

Beachside Resort & Residences

Hyatt Vacation Club at Windward Pointe, Key West

The Gates Hotel Key West Newly Renovated

Ibis Bay Beach Resort

Parrot Key Hotel & Villas

The Perry Hotel & Marina Key West

Southernmost Beach Resort

Oceans Edge Key West Resort, Hotel & Marina

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Frequently asked questions