Islamorada Hotels with a Pool

Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices

Check prices for these dates

Tonight
24 July - 25 July
Tomorrow
25 July - 26 July
This weekend
25 July - 27 July
Next weekend
1 Aug - 3 Aug

Islamorada Hotels with a Pool

Chesapeake Beach Resort
Relax on the beach with a tranquil ocean view and comfortable sun loungers.

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1490)
"We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!"
Michael
The price is AU$407
includes taxes & fees
10 Aug - 11 Aug
Chesapeake Beach Resort
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.

Top neighbourhoods in Islamorada

Islamorada showing a beach bar
Matecumbe map

Matecumbe

The Matecumbe neighbourhood offers attractions, such as Bud n' Mary's Dive Center and Florida Keys Brewing Co..

Venetian Shores map

Venetian Shores

The Venetian Shores neighbourhood offers attractions, such as Everglades National Park and Baker's Cay Resort Beach.

Lower Matecumbe Beach map

Lower Matecumbe Beach

Islamorada's Lower Matecumbe Beach neighbourhood offers attractions, including Sunset Drive Beach.

Seabreeze Trailer Park map

Seabreeze Trailer Park

Islamorada's Seabreeze Trailer Park neighbourhood has lots of places to visit, such as Everglades National Park and Baker's Cay Resort Beach.

Top landmarks in Islamorada

Theater of the Sea
Theater of the Sea

Theater of the Sea

Get lost in halls of wondrous fish and exotic marine mammals at Theater of the Sea, located 2.3 mi (3.7 km) from central Islamorada. Hotels.com travellers also say the area is family-friendly and that it has lots of nice beaches. If you'd also like to explore some of the parks in Islamorada, Islamorada County Park and Founders Park are both nearby.

See properties in Theater of the Sea
Anne's Beach
Anne's Beach

Anne's Beach

If you can't wait to get to the beach, you might enjoy a trip to Anne's Beach, located 8.8 mi (14.1 km) from central Islamorada. If you want to continue walking by the waves, head to Sunset Drive Beach located nearby.

See properties in Anne's Beach

Frequently asked questions

What are the best hotels with a pool in Islamorada?
According to guest reviews, The Caribbean Resort is one of the top Islamorada hotels with a pool. Individually decorated rooms and pool sun loungers are included in your stay too. Casa Morada is another visitor favourite where you can enjoy some poolside relaxation. To find other popular 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 Islamorada?
Coconut Palm Inn is one of the cheapest properties with a pool in Islamorada. It also offers a firepit and a marina. La Jolla Resort is another option where you can take a dip without dipping into your finances. Check out the range of great-value hotels in Islamorada with a pool from AU$131 and have more fun for less.
What is the best time to stay in a hotel with a pool in Islamorada?
If you want the warmest weather, plan your trip for August. The temperatures are around 29ºC to 30ºC at this time. January has the coolest temperatures between 20ºC and 22ºC. For a more relaxed setting and potentially cheaper Islamorada hotels with a pool, visit in October when it's quieter.
What hotels with a pool are closest to Theatre of the Sea?
With a beach view and a water view, Pelican Cove Resort & Marina is one of the closest hotels with a pool to Theatre of the Sea. Casa Morada is another option just a short drive away. Balance sightseeing with leisure when you book a hotel in Islamorada with a pool near this attraction.
Are there any hotels with a pool in Islamorada with parking?
With a pool, parking, designer toiletries and pool sun loungers, Casa Morada is a standout choice. You can also relax poolside or head out whenever you like at Islander Resort. For more options, check out the 2,187 Islamorada hotels with a pool and parking.