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
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 NT$5,720
NT$8,553 total
includes taxes & fees
Nov 17 - Nov 18
Amara Cay Resort
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1015)
"Wonderful 2 day girls trip. Everything was amazing!"
The price is NT$5,939
NT$8,440 total
includes taxes & fees
Dec 1 - Dec 2
Islander Resort
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 NT$7,312
NT$10,345 total
includes taxes & fees
Nov 12 - Nov 13
La Siesta Resort & Villas
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 NT$6,227
NT$9,161 total
includes taxes & fees
Nov 6 - Nov 7
Cheeca Lodge & Spa
Drop Anchor
3.0 star property
8.8 out of 10, Excellent, (1004)
"Is a beutifull place to relax ."
Drop Anchor
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 NT$11,910
NT$15,283 total
includes taxes & fees
Nov 18 - Nov 19
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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
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 NT$3,704
NT$5,208 total
includes taxes & fees
Nov 6 - Nov 7
Fisher Inn Resort & Marina
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 NT$6,105
NT$8,628 total
includes taxes & fees
Dec 1 - Dec 2
Islander Bayside Villas and Boatslips
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 NT$4,116
NT$4,630 total
includes taxes & fees
Nov 12 - Nov 13
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.