Find hotels with pools in Islamorada, FL from $122

Pick from 31 Islamorada Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Exterior
The Caribbean Resort
3.5 star property
10.0 out of 10, Exceptional, (134)
"What a wonderful resort in paradise. We stayed in the Bird of Paradise and it was perfect. Look out the window at the Atlantic Ocean. Would definitely come back again. 5 stars. "
The Caribbean Resort
Aerial view
Casa Morada
3.5 star property
9.4 out of 10, Exceptional, (350)
"Loved our stay! Unique property, we will be back again! Thank you!"
The price is $311
per night
May 14 - May 15
Casa Morada
Aerial view
Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (955)
"Beautiful place to get away with your family"
The price is $199
per night
Jun 2 - Jun 3
Pines & Palms Resort
Pool
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1002)
"Absolutely beautifully appointed room and patio. Our family loves this resort. "
The price is $287
per night
May 20 - May 21
Islander Resort
Pool
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1008)
"Beautiful property"
The price is $289
per night
May 23 - May 24
Cheeca Lodge & Spa
Exterior
Drop Anchor
3.0 star property
9.0 out of 10, Wonderful, (1003)
"We loved Drop Anchor! The property was perfect! The location, clean, quiet, beach, heated pool, tiki huts with adirondeck chairs and hammocks. Exactly, what we were looking for and thoroughly enjoyed."
The price is $153
per night
May 16 - May 17
Drop Anchor
Exterior
Islander Bayside Villas and Boatslips
3.5 star property
9.0 out of 10, Wonderful, (335)
"Lovely sister property to the Islander - Resort; the, Islander Bayside resort Townhomes are wonderful. The Green Tuttle Inn. And the NEST across overseas highway great spirits & food. kitchens open until 10pm. 7 am green turtle breakfast. Or Mangrove Mike’s is a short walk North for breakfast. First night we walked to Lorelei, (15 minutes walk) for sunset. Best spot. This property is Slightly less than 2 miles NORTH from Bud and Mary’s marina and Lazy Days. Ideal for family or larger...
The price is $294
per night
Jun 3 - Jun 4
Islander Bayside Villas and Boatslips
Beach
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1317)
"This was my first time in the Keys and this hotel did not disappoint. The property is beautiful, staff is super friendly and helpful and the location is perfect if you’re planning on checking out other islands. Islamorada is just under 2 hours from Key West so it’s easily drivable. I would absolutely stay here again. "
The price is $199
per night
May 19 - May 20
Chesapeake Beach Resort
Outdoor pool
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1247)
"The resort was absolutely beautiful and the staff go above and beyond. The room key bracelets were so convenient and so cute to wear. We even got to keep them as souvenirs. Definitely the best place I have ever stayed. "
The price is $270
per night
May 20 - May 21
Amara Cay Resort
Surfing/boogie boarding
La Siesta Resort & Villas
4.0 star property
8.6 out of 10, Excellent, (1003)
"It was excellent, but could use a microwave in room"
The price is $293
per night
May 21 - May 22
La Siesta Resort & Villas
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Islamorada Hotels with a Pool information

 

Hotels with a Pool in Islamorada

31

Highest price
$294
Cheapest price
$122
Number of guest reviews
9,206
Total number of hotels in Islamorada
2,122

 

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 56 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. Cheeca Lodge & Spa: Offers a private beach, 3 outdoor pools, and 3 restaurants. Islander Resort: Provides a private beach, 3 outdoor pools, and cabanas (surcharge). Drop Anchor: Features free self parking, an outdoor pool, and complimentary bicycles. Hadley Resort and Marina: Offers daily, an outdoor pool, and complimentary bicycles.
How many pool hotels should I expect to find in Islamorada?
Expedia’s 56 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.

Recent reviews of Islamorada hotels
Expedia verified reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

5/5 Excellent
"This was my first time in the Keys and this hotel did not disappoint. The property is beautiful, staff is super friendly and helpful and the location is perfect if you’re planning on checking out other islands. Islamorada is just under 2 hours from Key West so it’s easily drivable. I would absolutely stay here again. "
A verified traveler stayed at Chesapeake Beach Resort
Posted 3 hours ago
Chesapeake Beach Resort