The Best Hotels with a Pool in Long Key, FL from ₩283,280 in 2026 | Expedia

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Long Key Hotels with a Pool

Tonight

Jun 13 - Jun 14

Tomorrow

Jun 14 - Jun 15

Next weekend

Jun 19 - Jun 21

In two weeks

Jun 26 - Jun 28

Our top choices for Long Key hotels with a pool

View from property

Lime Tree Bay Resort

Long Key

A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.

₩288,781 total

includes taxes & fees

Jul 6 - Jul 7

Outdoor pool, sun loungers

Edgewater Lodge

Long Key

Dive into crystal waters and soak in ocean vistas at this serene beachfront hotel featuring a sparkling outdoor pool and loungers.

₩520,786 total

includes taxes & fees

Jun 28 - Jun 29

Apartment (3 Bedrooms) | Interior

Florida Keys Getaway w/ Stunning Ocean Views

Long Key

₩1,586,450 total

includes taxes & fees

Jun 14 - Jun 15

Outdoor pool

Treasure Harbor

Islamorada

₩434,640 total

includes taxes & fees

Jun 21 - Jun 22

Exterior

Ragged Edge Resort & Marina

Islamorada

Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.

₩321,067 total

includes taxes & fees

Jun 14 - Jun 15

2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

Chesapeake Beach Resort

Matecumbe

Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.

₩391,813 total

includes taxes & fees

Jun 18 - Jun 19

Exterior

Breezy Palms Resort

Matecumbe

Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.

₩283,280 total

includes taxes & fees

Jul 1 - Jul 2

Outdoor pool, pool umbrellas, sun loungers

Amara Cay Resort

Matecumbe

Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.

₩455,444 total

includes taxes & fees

Jun 24 - Jun 25

View all properties

Choose what matters most at hotels with a pool in Long Key

Breakfast included

4 stars

Top Long Key Hotel Reviews

Amara Cay Resort

Amara Cay Resort

8/10 Good

"I have mixed reviews. The staff was very helpful, especially the lobby bartender, Marcus. The grounds and the pool area are very nicely maintained. The location is very close to Bud and Mary's marina, where my husband booked a half day fishing charter. Also, very close to the Midway Cafe- excellent coffee and key lime pie! My main complaint would be the rooms. They definitely need some upgrades. Our room smelled musty and the hallway did also. Mildew stains on the patio curtains. Also, this facility allows dogs, so be aware of that. Our next door neighbors had a large dog that started barking in the middle of the night for ten minutes straight and my husband had to go bang on their door to get it to stop. Overall, a good, but not awesome stay for us."

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent

"Nice property- very clean, helpful and kind staff, and we loved the amenities. Paddleboarding and kayaking was incredible! This is a hidden little gem in FL Keys. We stayed off the main property in the townhouses along the canal, and it felt so private. It was nice to be able to leave the main property and have some quiet time but also use all the amenities at the main property when we wanted. We would definitely stay again!!"

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent

"This place was great! Very private, great amenities, staff, location, and accessible! Has everything you need for intimate location Oceanview is stellar, you can walk right into the ocean and relax with provided chairs, umbrellas, and towels. They have breakfast included with all breakfast types from made to order omelette, French toasts, pancakes, waffles, bagels, etc.y only complaint is the smell of grease inside the breakfast location that stays with you as soon as you walk in and you have to change your clothes right after. Also, wish they had a restaurant on property to order food."

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

10/10 Excellent

"This hotel was well maintained and the staff was great! Out of the choices that are available in this area of the Keys, it would be hard to find a better place to stay - excellent pool overlooking the water, a small bay area, poolside service and bar, clean facilities and a great staff."

Frequently asked questions

What's it like visiting Long Key?

If lounging next to a pool is your idea of the perfect getaway, you may want to consider relaxing Long Key, which has 10 places to stay with pools. While you're here, you can explore attractions like Long Key State Park and Fiesta Key, and then unwind poolside at one of the accommodations in Long Key that guests like for their pools.

What are some accommodations with pools in Long Key?

Lime Tree Bay Resort: Features a private beach, 3 outdoor pools, and free self parking. Fiesta Key RV Resort: Offers free self parking, an outdoor pool, and sun loungers. Edgewater Lodge: Provides free self parking, an outdoor pool, and complimentary wireless internet access. Cheeca Lodge & Spa: Features a private beach, 3 outdoor pools, and 3 restaurants. Chesapeake Beach Resort: Offers a private beach, 2 outdoor pools, and daily.

How many hotels with pools will I be able to find in Long Key?

Expedia has 10 hotels in Long Key for your poolside break.

What is there to see and do in Long Key?

The picturesque setting of Fiesta Key showcases the area's natural beauty. Discover sights such as Long Key State Park during your stay. The sunsets, beaches, and fishing are just some of the things to enjoy while you're in the area.

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

Taking into account the local weather in Long Key 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 72°F. Average annual precipitation for Long Key is 36 inches.

Explore a world of travel with Expedia

More ways to book

Book Hotels with a Pool in Long Key on Expedia.com

c233d13d-e409-48ef-95bd-37514b2197de8ed78dda-6f4a-43ba-92bc-0bb227f69295