Find Hotels with a Pool in Islamorada, FL from CA $168

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May 15 - May 16
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May 16 - May 17
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May 17 - May 19
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May 24 - May 26

Top Islamorada Hotels with a Pool

The Caribbean Resort
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
Casa Morada
Property grounds
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 CA $401
CA $669 total
includes taxes & fees
May 27 - May 28
Casa Morada
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, (955)
"Beautiful place to get away with your family"
The price is CA $231
CA $324 total
includes taxes & fees
Jun 6 - Jun 7
Pines & Palms Resort
Islander Resort
3 outdoor pools, cabanas (surcharge), pool umbrellas
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 CA $327
CA $443 total
includes taxes & fees
May 22 - May 23
Islander Resort
Cheeca Lodge & Spa
Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1005)
"Beautiful property"
The price is CA $545
CA $697 total
includes taxes & fees
Jun 10 - Jun 11
Cheeca Lodge & Spa
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Good"
The price is CA $209
CA $283 total
includes taxes & fees
May 16 - May 17
Drop Anchor
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers
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 CA $392
CA $516 total
includes taxes & fees
May 27 - May 28
Islander Bayside Villas and Boatslips
Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1322)
"Guy making omelette was awesome"
The price is CA $272
CA $360 total
includes taxes & fees
May 19 - May 20
Chesapeake Beach Resort
Amara Cay Resort
Exterior
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1243)
"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 CA $394
CA $519 total
includes taxes & fees
May 20 - May 21
Amara Cay Resort
La Siesta Resort & Villas
Aerial view
La Siesta Resort & Villas
4.0 star property
8.6 out of 10, Excellent, (1000)
"It was excellent, but could use a microwave in room"
The price is CA $400
CA $525 total
includes taxes & fees
May 19 - May 20
La Siesta Resort & Villas
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Islamorada Hotels with a Pool information

 

Hotels with a Pool in Islamorada

31

Highest price
CA $545
Cheapest price
CA $168
Number of guest reviews
9,197
Total number of hotels in Islamorada
2,125

 

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 57 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 57 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 in Islamorada
Expedia verified reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

5/5 Excellent
"Guy making omelette was awesome"
A verified traveller stayed at Chesapeake Beach Resort
Posted 22 hours ago
Chesapeake Beach Resort