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.

Amara Cay Resort
Outdoor pool
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1228)
"Loved it! We had a beautiful view of the water. The rooms were large and clean. I would recommend if staying in Islamorada. "
The price is SAR 673
SAR 987 total
includes taxes & fees
17 Nov - 18 Nov
Amara Cay Resort
Islander Resort
Pool
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1015)
"Wonderful 2 day girls trip. Everything was amazing!"
The price is SAR 699
SAR 976 total
includes taxes & fees
1 Dec - 2 Dec
Islander Resort
La Siesta Resort & Villas
Outdoor pool
La Siesta Resort & Villas
4.0 star property
8.6 out of 10, Excellent, (1011)
"Loved my stay here and will definitely come back! My room had some things that need repaired or updated (like broken blinds and cracks/water damage on the wall under the windows) but barely noticeable really compared to how great everything else was! I had a bottom floor room with a sliding door that goes out to a seating area and ocean view! The ladies at the front desk were super friendly too! The only thing that irked me was on check-out day the cleaning lady was sitting outside my sliding...
The price is SAR 645
SAR 953 total
includes taxes & fees
12 Nov - 13 Nov
La Siesta Resort & Villas
Cheeca Lodge & Spa
Pool
Cheeca Lodge & Spa
5.0 star property
9.0 out of 10, Wonderful, (1019)
"Spectacular resort. Been before, will return again. Fly into Key West and drive up."
The price is SAR 667
SAR 992 total
includes taxes & fees
1 Dec - 2 Dec
Cheeca Lodge & Spa
Drop Anchor
Pool
Drop Anchor
3.0 star property
8.8 out of 10, Excellent, (1004)
"Is a beutifull place to relax ."
The price is SAR 1,153
SAR 1,402 total
includes taxes & fees
12 Nov - 13 Nov
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pool
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3.0 star property
8.0 out of 10, Very Good, (1006)
"The entire staff was very friendly "
The price is SAR 1,401
SAR 1,777 total
includes taxes & fees
18 Nov - 19 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort
Outdoor pool
Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (974)
"Place was under heavy construction, when booking stay know one mentioned the whole resort is under reconstruction. Besides the construction the location was beautiful setting "
Pines & Palms Resort
Fisher Inn Resort & Marina
Pool
Fisher Inn Resort & Marina
3.5 star property
7.6 out of 10, Good, (1004)
"Great sta, can't wait to get back. Staff helped with fishing charter and restaurant recommendations. Private beach meant we could spread out and relax! "
The price is SAR 504
SAR 673 total
includes taxes & fees
6 Nov - 7 Nov
Fisher Inn Resort & Marina
Islander Bayside Villas and Boatslips
Pool
Islander Bayside Villas and Boatslips
3.5 star property
8.8 out of 10, Excellent, (354)
"Wonderful easy to stay resort, just perfect! "
The price is SAR 718
SAR 997 total
includes taxes & fees
1 Dec - 2 Dec
Islander Bayside Villas and Boatslips
Coconut Cove Resort and Marina
Outdoor pool
Coconut Cove Resort and Marina
2.5 star property
7.4 out of 10, Good, (681)
"Great spot. Beautiful views. Great pool. Staff friendly "
The price is SAR 485
SAR 534 total
includes taxes & fees
11 Nov - 12 Nov
Coconut Cove Resort and Marina
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.
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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 33 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.
What are some accommodations with pools in Islamorada?
Chesapeake Beach Resort: Features a private beach, 2 outdoor pools, and sun loungers. Drop Anchor: Offers free self parking, an outdoor pool, and complimentary bicycles. Fisher Inn Resort & Marina: Provides a private beach, a pool, and daily. Sands of Islamorada: Features free self parking, a pool, and complimentary wireless internet access. Islander Bayside Villas and Boatslips: Offers free self parking, an outdoor pool, and complimentary wireless internet access.
How many pool hotels should I expect to find in Islamorada?
Expedia’s 33 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.