Find Hotels with a Pool in Islamorada, FL

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Compare Islamorada Hotels with a Pool 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, (1209)
"Good stop on the way to kw."
The price is AED 1,527
AED 1,962 total
includes taxes & fees
26 Dec - 27 Dec
Amara Cay Resort
Islander Resort
Pool

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1004)
"The space is currently ongoing construction but don’t let that stop you from staying. Beautiful location and friendly staff from the initial security guard interaction onward. Would love to come back when the construction is complete "
The price is AED 951
AED 1,302 total
includes taxes & fees
23 Dec - 24 Dec
Islander Resort
La Siesta Resort & Villas
Outdoor pool

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1000)
"Great resort!!"
La Siesta Resort & Villas
Cheeca Lodge & Spa
Pool

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1005)
"Excellent vacation resort"
The price is AED 966
AED 1,335 total
includes taxes & fees
8 Jan - 9 January 2025
Cheeca Lodge & Spa
Drop Anchor
Pool

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1001)
"The location was beautiful, rooms should be updated. My biggest complaint is a paid for two rooms, same price for both, but one was very much smaller than the other and no balcony in that same room either ?!?!"
The price is AED 469
AED 656 total
includes taxes & fees
23 Dec - 24 Dec
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, (1008)
"Excellent and amazing property. I love this resort. Will be back"
The price is AED 1,425
AED 1,847 total
includes taxes & fees
5 Jan - 6 January 2025
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 location in the Middle Keys and close to all of the cool hang-outs! Also very clean, has a nice pool and my room had the best balcony view ever!!!"
The price is AED 746
AED 959 total
includes taxes & fees
8 Jan - 9 January 2025
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, (357)
"Wonderful easy to stay resort, just perfect! "
The price is AED 1,044
AED 1,406 total
includes taxes & fees
20 Jan - 21 January 2025
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, (684)
"I like it"
The price is AED 547
AED 616 total
includes taxes & fees
23 Dec - 24 Dec
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 21 places to stay with pools. During your trip, you can explore sights such as Everglades National Park and Florida Keys Brewing Co., 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.
How many pool hotels should I expect to find in Islamorada?
Expedia’s 21 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.