Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

Tonight
Mar 25 - Mar 26
Tomorrow
Mar 26 - Mar 27
This weekend
Mar 28 - Mar 30
Next weekend
Apr 4 - Apr 6

Compare Islamorada Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1208)
"Great staff"
The price is NT$10,379
NT$13,868 total
includes taxes & fees
Mar 30 - Mar 31
Amara Cay Resort
Islander Resort
Exterior

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1004)
"Overall, the resort was beautiful! Loved the decor. It is expensive and then you are charged a resort fee. Resort activities are great for families and all the kids running around including people not staying there. Not fair for older people to be charged. We loved the porch on our room(needed a key to get in that way). Bathroom is very small. Restaurants are expensive and need more variety on menu. Lots of great dining in area."
The price is NT$10,542
NT$13,941 total
includes taxes & fees
Apr 6 - Apr 7
Islander Resort
La Siesta Resort & Villas
Outdoor pool, sun loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1000)
"Such a nice, cute and fun little place on Islamorada! Highly recommend! "
The price is NT$9,883
NT$13,311 total
includes taxes & fees
Mar 30 - Mar 31
La Siesta Resort & Villas
Cheeca Lodge & Spa
Private beach, sun loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1050)
"Wonderful stay - beautiful grounds "
The price is NT$16,480
NT$20,770 total
includes taxes & fees
Apr 6 - Apr 7
Cheeca Lodge & Spa
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1001)
"The front desk guy was so nice, really just a very friendly guy and I appreciate that. The room was a bit hot -the ac wasn’t working right, it was blowing but not cold air unfortunately. The room itself and bathroom were super cute, the bed and pillows were very comfy, it was nice and quiet and I rested very well other than being a little hot. "
The price is NT$8,544
NT$10,768 total
includes taxes & fees
Mar 26 - Mar 27
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3 outdoor pools, a heated pool, pool umbrellas, sun loungers

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

3.5 star property
8.0 out of 10, Very Good, (1008)
"Front desk staff was very helpful. There were multiple lounge chairs at the water’s edge both full sun and shade. Manatees in the marina. Tiki Bar made for a fun friendly evening. Enjoyed our stay so much we didn’t want to leave!"
The price is NT$12,043
NT$15,741 total
includes taxes & fees
Apr 1 - Apr 2
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort
Outdoor pool, a heated pool, pool umbrellas, sun loungers

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (981)
"3/2025 appears new, very clean. "
The price is NT$10,536
NT$13,673 total
includes taxes & fees
Mar 30 - Mar 31
Pines & Palms Resort
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
7.8 out of 10, Good, (1002)
"It was all around great "
The price is NT$6,709
NT$8,626 total
includes taxes & fees
Apr 2 - Apr 3
Fisher Inn Resort & Marina
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (360)
"It was ok I suppose. Not really worth the money. "
The price is NT$13,176
NT$16,902 total
includes taxes & fees
Apr 7 - Apr 8
Islander Bayside Villas and Boatslips
Coconut Cove Resort and Marina
Outdoor pool, sun loungers

Coconut Cove Resort and Marina

2.5 star property
7.6 out of 10, Good, (746)
"The rooms are a bit dated, but everything was clean and secure. The grounds were immaculately maintained and we spent a fair amount of time at the pool and lounging on the beach. Great central location, quick drive to many bars and restaurants. We would definitely stay here again!"
The price is NT$9,215
NT$10,366 total
includes taxes & fees
Mar 26 - Mar 27
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. Fisher Inn Resort & Marina: Offers a private beach, a pool, and daily. Drop Anchor: Provides free self parking, an outdoor pool, and complimentary bicycles. 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 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.