Hotels with a Pool in Islamorada

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Hotels with a Pool in Islamorada

Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1479)
$183 nightly
The price is $206
Aug 3 - Aug 4
Total includes taxes and fees
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 neighborhoods in Islamorada

Islamorada showing a beach bar
Matecumbe map

Matecumbe

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

Venetian Shores map

Venetian Shores

The Venetian Shores neighborhood 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 neighborhood offers attractions including Sunset Drive Beach.

Seabreeze Trailer Park map

Seabreeze Trailer Park

Islamorada's Seabreeze Trailer Park neighborhood has a host 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

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 travelers also say the area is family-friendly and 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
Theater of the Sea

Frequently asked questions

What are the best hotels with a pool in Islamorada?
One of the best Islamorada hotels with a pool according to guest reviews is The Caribbean Resort. Make use of a nearby waterfront and on-site ecotour services here. Pool days will also become part of your daily routine at Casa Morada, another highly rated option.
What are the cheapest hotels with a pool in Islamorada?
It's a breeze to find some of the cheapest hotels in Islamorada with a pool from $150 for your next getaway. One of the most affordable is Coconut Palm Inn. It offers a barbecue grill and a terrace too. La Jolla Resort is another option where you can chill by the pool without worrying about your wallet.
What is the best time to stay in a hotel with a pool in Islamorada?
The best time to stay in a Islamorada hotel with a pool depends on the type of getaway you're after. Visit during a peak period if you want to jump right into the fun and enjoy the vibrant energy. Alternatively, choose a quieter time if you'd like a more relaxed poolside experience and potentially cheaper hotels.
What hotels with a pool are closest to Theater 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 Theater of the Sea. Casa Morada is another option just a short drive away. Balance sightseeing with leisure when you stay in a hotel in Islamorada with a pool near this attraction.
Are there any hotels with a pool in Islamorada with parking?
There are 2,179 Islamorada hotels with a pool and parking. Book a room at Casa Morada, which has designer toiletries and pool sun loungers. Islander Resort also combines the ease of parking with the perks of a pool.
Are all taxes and fees included in the Islamorada hotel prices shown on Hotels.com?
Hotels.com provide upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.