Find Hotels with a Pool in Islamorada, FL

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Pick from 31 Islamorada Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Exterior
The Caribbean Resort
3.5 star property
10.0 out of 10, Exceptional, (136)
"Landscaped beautifully. Weber grills to barbecue. The rooms were decorated magnificently and the wrap around porch was terrific."
The Caribbean Resort
Aerial view
Casa Morada
3.5 star property
9.4 out of 10, Exceptional, (353)
"Loved this little quiet hidden property."
The price is AED 1,186
AED 1,587 total
includes taxes & fees
28 May - 29 May
Casa Morada
Aerial view
Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (955)
"Beautiful place to get away with your family"
The price is AED 584
AED 817 total
includes taxes & fees
3 Jun - 4 Jun
Pines & Palms Resort
Pool
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1002)
"The property was amazing! We loved our stay. The only concern is that the pools need work. Lots of small tiles missing."
The price is AED 879
AED 1,169 total
includes taxes & fees
30 May - 31 May
Islander Resort
Pool
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1006)
"Rooms are very quiet. We had two small children and we were worried we would hear neighbors or we would bother them but you couldn’t hear anything in next room. Hotel was fully book3d "
The price is AED 1,172
AED 1,537 total
includes taxes & fees
27 May - 28 May
Cheeca Lodge & Spa
Exterior
Drop Anchor
3.0 star property
9.0 out of 10, Wonderful, (1002)
"The view and nice area to sit and watch. "
The price is AED 683
AED 881 total
includes taxes & fees
27 May - 28 May
Drop Anchor
Exterior
Islander Bayside Villas and Boatslips
3.5 star property
9.0 out of 10, Wonderful, (336)
"I have never encountered a staff so helpful and pleasant Thank you"
The price is AED 996
AED 1,298 total
includes taxes & fees
29 May - 30 May
Islander Bayside Villas and Boatslips
Beach
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1326)
"Great Place, very friendly staff and hosts. Free breakfast sin sunrise room was great. Clean rooms and pools and beaches. Cleaning services were prompt and good, Hotel was quiet and clean. But upon checkout we noticed a 40$ daily service charge per day for Resort Fees. A little surprised, because that was in addition to the hotel daily charge and Tax"
The price is AED 841
AED 1,093 total
includes taxes & fees
29 May - 30 May
Chesapeake Beach Resort
Outdoor pool
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1243)
"The layout is perfect. Very clean and spacious rooms"
The price is AED 1,141
AED 1,447 total
includes taxes & fees
12 Jun - 13 Jun
Amara Cay Resort
Surfing/boogie boarding
La Siesta Resort & Villas
4.0 star property
8.6 out of 10, Excellent, (1001)
"Beautiful property with amazing ocean views great pool area"
The price is AED 1,208
AED 1,562 total
includes taxes & fees
2 Jun - 3 Jun
La Siesta Resort & Villas
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See all available properties in Islamorada
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.

Frequently asked questions

What's it like visiting Islamorada?
If taking it easy by the pool is your idea of the perfect getaway, you might want to think about relaxing Islamorada, which offers 57 places to stay with pools. During your trip, you can explore sights such as Everglades National Park and Bud n’ Mary’s Dive Center, and then relax and unwind poolside at one of the accommodations in Islamorada that guests like for their pools.
How many pool hotels should I expect to find in Islamorada?
Expedia’s 57 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Explore places like Everglades National Park while you’re in Islamorada. Enjoy a stroll along the shore at Anne’s Beach and Sunset Drive Beach. Islamorada appeals to visitors with its beautiful ocean views and top seafood restaurants.
When is the best time to book a hotel with a pool in Islamorada?
Taking into account the local weather in Islamorada 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 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.

Recent reviews of Islamorada hotels
Expedia verified reviews

Casa Morada

Casa Morada

5/5 Excellent
"Loved this little quiet hidden property."
A verified traveler stayed at Casa Morada
Posted 2 days ago
Casa Morada