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, (354)
"Good quiet location in Islamorada - just the job"
The price is SAR 1,211
SAR 1,621 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Casa Morada
Aerial view
Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (956)
"Beautiful place to get away with your family"
The price is SAR 671
SAR 917 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Pines & Palms Resort
Pool
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1005)
"My only drawback was the kids after midnight jumping off the fountain into the pool. It just seemed like there was less security. "
The price is SAR 971
SAR 1,275 total
includes taxes & fees
29 Jum. I - 30 Jum. I
Islander Resort
Pool
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1014)
"Lovely experience. A place we will come back to visit. "
The price is SAR 1,196
SAR 1,569 total
includes taxes & fees
29 Jum. I - 30 Jum. I
Cheeca Lodge & Spa
Exterior
Drop Anchor
3.0 star property
9.0 out of 10, Wonderful, (1005)
"Great location with friendly staff. Hot water was nonexistent for our three day visit. Lock on sliding balcony door would not lock. Would stay here again in spite of these conditions."
The price is SAR 697
SAR 900 total
includes taxes & fees
4 Jum. II - 5 Jum. II
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 SAR 1,077
SAR 1,392 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Islander Bayside Villas and Boatslips
Beach
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1339)
"We really enjoyed it, staff was very nice and property was nice and clean. It has 2 pools and beach access. We would definitely come back!"
The price is SAR 971
SAR 1,243 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Chesapeake Beach Resort
Outdoor pool
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1245)
"Small but very comfortable resort in Islamorada. Great resort activities available and communicative, helpful staff. The wait staff at the restaurant were fantastic. Well priced resort experiences such as snorkeling and professional photography! Shout out to Captain Ken, his wife, and Javier the photographer! "
The price is SAR 1,332
SAR 1,655 total
includes taxes & fees
27 Jum. II - 28 Jum. II
Amara Cay Resort
Surfing/boogie boarding
La Siesta Resort & Villas
4.0 star property
8.6 out of 10, Excellent, (1004)
"Like the bracelets. Convenient way to get in and out of the room. Hassle free ordering food, checking in & out. Wish there were more indoor activities though, it was quite gloomy when we stayed so nothing much to do when in the hotel. But I love the peace & quiet. Very nice hotel. Overall, we loved our room, the staff and the hotel. "
The price is SAR 1,265
SAR 1,584 total
includes taxes & fees
27 Jum. II - 28 Jum. II
La Siesta Resort & Villas
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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

Chesapeake Beach Resort

Chesapeake Beach Resort

5/5 Excellent
"We really enjoyed it, staff was very nice and property was nice and clean. It has 2 pools and beach access. We would definitely come back!"
A verified traveler stayed at Chesapeake Beach Resort
Posted 1 day ago
Chesapeake Beach Resort