Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

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, (1210)
"Excellent "
The price is AED 1,099
AED 1,480 total
includes taxes & fees
26 Jan - 27 Jan
Amara Cay Resort
Islander Resort
Pool

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1004)
"Best 5 star resort in Florida keys, from the rooms, pools, beach area and staff. The staff at the hotel were so friendly, helpful and generous. A kind member of staff gave us an extra 25 cent for the laundry after helping to explain how it works. The rooms had modern facilities but the beautiful layout was classical beach house designed to make you feel completely relaxed. The pools were all heated/temperature controlled, so even if it was slight cold outside you can still enjoy a swim. Out of...
The price is AED 1,055
AED 1,418 total
includes taxes & fees
23 Jan - 24 Jan
Islander Resort
La Siesta Resort & Villas
Outdoor pool

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1001)
"I understood that the place was pet friendly. However, nowhere in the booking process was I made aware that I would have to pay $50.00 per dog per night for the stay. Cost an extra $200.00 upon arrival. Somewhere in the process this was not made clear in any way that I saw. "
The price is AED 1,017
AED 1,387 total
includes taxes & fees
26 Jan - 27 Jan
La Siesta Resort & Villas
Cheeca Lodge & Spa
Pool

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1025)
"Stunning views and property, comfy and quiet rooms.Excellent service especially the tiki bar! "
The price is AED 1,098
AED 1,483 total
includes taxes & fees
23 Jan - 24 Jan
Cheeca Lodge & Spa
Drop Anchor
Pool

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1001)
"Good value for the money. Enjoyed using the kayaks and paddle boards. Friendly staff. Very good location on the water."
The price is AED 701
AED 917 total
includes taxes & fees
23 Jan - 24 Jan
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pool

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

3.5 star property
8.0 out of 10, Very Good, (1008)
"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 AED 1,432
AED 1,855 total
includes taxes & fees
29 Jan - 30 Jan
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 "
The price is AED 584
AED 942 total
includes taxes & fees
28 Jan - 29 Jan
Pines & Palms Resort
Fisher Inn Resort & Marina
Pool

Fisher Inn Resort & Marina

3.5 star property
7.8 out of 10, Good, (1001)
"We had such a great experience! Nice room with a great view, friendly staff, dog friendly. The bikes, kayaks and paddle boards were a nice touch too!"
The price is AED 768
AED 983 total
includes taxes & fees
26 Jan - 27 Jan
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, (358)
"We booked here because of the full kitchen plus living areas; the kitchen was pretty sparse regarding cookware/appliances, but the front desk bent over backwards to get us the missing items we requested. One of the selling points was access to their resort property, just up the street. However, that property was almost deserted due to a lot of construction work. The resort pool was closed (the Bayside Villas pool was open). Overall this was a pleasant stay for us."
The price is AED 1,137
AED 1,511 total
includes taxes & fees
2 Feb - 3 Feb
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, (699)
"The property itself is amazing. The room was very clean and comfortable. The staff and property manager are incredible - super friendly, helpful and accommodating. We’d definitely stay again!"
The price is AED 694
AED 781 total
includes taxes & fees
23 Jan - 24 Jan
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 22 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 22 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.