A beach with white lounge chairs, a covered pavilion, and palm trees.

Hotels with Swimming Pool in Islamorada, Florida

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Check availability on Islamorada Hotels with Swimming Pool

Our top choices for Islamorada hotels with a pool

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

1. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,170 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is P11,412
P17,495 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,516 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is P11,546
P17,646 total
includes taxes & fees
Nov 16 - Nov 17
Cheeca Lodge & Spa
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

3. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,823 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is P10,224
P15,085 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Beach Resort
A swimming pool with palm trees and lounge chairs.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,331 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is P10,704
P16,699 total
includes taxes & fees
Nov 16 - Nov 17
Amara Cay Resort
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.

5. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
The price is P8,024
P10,819 total
includes taxes & fees
Nov 18 - Nov 19
La Jolla Resort
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the ocean.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (313 reviews)
  • cleanliness
    Sparkling pools welcome island adventurers to this oceanfront sanctuary with marina access and private beach lounging areas.
The price is P13,195
P19,502 total
includes taxes & fees
Nov 29 - Nov 30
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

7. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (309 reviews)
  • cleanliness
    Splash into vacation mode at a Florida Keys gem with 24-hour pool access for endless aquatic adventures.
The price is P10,763
P12,108 total
includes taxes & fees
Nov 15 - Nov 16
Coconut Cove Resort and Marina
A poolside area with lounge chairs, a barbecue grill, and a view of the ocean.

8. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
The price is P10,655
P15,500 total
includes taxes & fees
Nov 15 - Nov 16
Pines & Palms Resort
Two people floating on inflatable rings in a clear pool.

9. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
The price is P9,844
P15,732 total
includes taxes & fees
Nov 17 - Nov 18
La Siesta Resort & Villas
A waterfront property with a pool, palm trees, and a white building with balconies.

10. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
  • cleanliness
    Poolside paradise in the heart of Matecumbe beckons with loungers under shady umbrellas.
The price is P17,882
P24,774 total
includes taxes & fees
Dec 1 - Dec 2
Bayside Villas by Islander Resort
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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Choose what matters most at hotels with a pool in Islamorada

Breakfast included
Hot tub

Hotels with pools and free breakfast in Islamorada

A beach with palm trees and lounge chairs.
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1823)
The price is P10,224
P15,085 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Beach Resort
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Hotels with pools and hot tubs in Islamorada

A hotel courtyard with palm trees, a tiled walkway, and a building entrance.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1516)
The price is P11,546
P17,646 total
includes taxes & fees
Nov 16 - Nov 17
Cheeca Lodge & Spa
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4-star hotels with pools in Islamorada

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1331)
The price is P10,704
P16,699 total
includes taxes & fees
Nov 16 - Nov 17
Amara Cay Resort
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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Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The room was very clean and comfortable, my only issue was it was close to the road so all you hear is road traffic. I asked to move rooms but we weren’t able to. The breakfast was nice- homemade omelet and waffles, a selections of items to toast. The bar tender Jose was super nice and very helpful as well as maintenance man Douglas- he was super Friendly. We thought the amenities were great and we would totally stay again!"
Wendy Gail 6-night trip
Posted 8 hours ago
Chesapeake Beach Resort

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 125 places to stay with pools. During your trip, you can explore sights such as Bud n' Mary's Dive Center and Robbie's of Islamorada, 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 daily. Fisher Inn Resort & Marina: Offers a private beach, a pool, and daily. Drop Anchor: Provides free self parking, an outdoor pool, and complimentary bicycles. Bayside Villas by Islander Resort: Features 3 restaurants, an outdoor pool, and free self parking.
How many pool hotels should I expect to find in Islamorada?
Expedia's 125 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Make a point to visit attractions like Anne's Beach and MoradaWay Arts & Cultural District. Discover sights such as Bud n' Mary's Dive Center, Robbie's of Islamorada, and Fiesta Key during your stay. 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.

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