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

4.0 star property
8.8 out of 10, Excellent, (1217)
"A beautiful property conveniently located in the Keys!"
The price is SAR 950
SAR 1,318 total
includes taxes & fees
8 Jan - 9 January 2025
Amara Cay Resort

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1003)
"Amazing property! Great service, food & drinks! A lot of workers on site so a bit noisy this weekend It’s going to be spectacular once they finish. "
The price is SAR 1,018
SAR 1,382 total
includes taxes & fees
20 Jan - 21 January 2025
Islander Resort

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1002)
"Cute little property with nice staff. Not much in terms of dining options on property but plenty off property. Can use facilities at two other sister properties. This is the chill one. Bathrooms could use maintenance and an update. Couch was kinda gross too. "
The price is SAR 1,198
SAR 1,597 total
includes taxes & fees
5 Jan - 6 January 2025
La Siesta Resort & Villas

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1008)
"Quick relaxing getaway before the holidays. The only complaint I would have is the coffee in the rooms was not the best and there was no coffee in the lobby so you had no choice but to go to the restaurant for coffees which was inconvenient. Otherwise, the food was amazing and the coffee at the restaurant was great."
The price is SAR 966
SAR 1,340 total
includes taxes & fees
8 Jan - 9 January 2025
Cheeca Lodge & Spa

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1001)
"This place had an amazing view and sunrise will most definitely me back to this place "
The price is SAR 533
SAR 731 total
includes taxes & fees
8 Jan - 9 January 2025
Drop Anchor

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 star property
8.0 out of 10, Very Good, (1010)
"Was great for a resort. Onsite restaurants have great food and amazing views. Contstant piped in music (all throughout the resort— on the beaches, the pools, the walkways, etc) was a downside but they might be par for the course on a resort. Biggest downside was that there is no hot tub on the premises. This might change as some of the resort is still under construction. Biggest upside is the amazing views and the wonderful staff. Everyone was not only polite, but helpful, and friendly. "
The price is SAR 1,457
SAR 1,888 total
includes taxes & fees
9 Jan - 10 January 2025
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, (1002)
"Amazing property to stay in isla morada, the staff was super friendly and helpful and the hotel is immaculate. This hotel is a must! "
The price is SAR 763
SAR 981 total
includes taxes & fees
8 Jan - 9 January 2025
Fisher Inn Resort & Marina

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 SAR 1,078
SAR 1,450 total
includes taxes & fees
20 Jan - 21 January 2025
Islander Bayside Villas and Boatslips

Coconut Cove Resort and Marina

2.5 star property
7.4 out of 10, Good, (685)
"I like it"
The price is SAR 747
SAR 841 total
includes taxes & fees
3 Jan - 4 January 2025
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.