Find Hotels with a Pool in Islamorada, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

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, (1,162 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is AED 658
AED 1,009 total
includes taxes & fees
15 Nov - 16 Nov
Islander Resort
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,810 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is AED 532
AED 805 total
includes taxes & fees
10 Nov - 11 Nov
Chesapeake Beach Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.

3. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,511 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is AED 666
AED 1,018 total
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.

4. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
The price is AED 460
AED 621 total
includes taxes & fees
18 Nov - 19 Nov
La Jolla Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

5. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (305 reviews)
  • cleanliness
    Splash into vacation mode at a Florida Keys gem with 24-hour pool access for endless aquatic adventures.
The price is AED 621
AED 698 total
includes taxes & fees
15 Nov - 16 Nov
Coconut Cove Resort and Marina
A resort pool with palm trees, beach chairs, and umbrellas.

6. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,333 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is AED 599
AED 942 total
includes taxes & fees
15 Nov - 16 Nov
Amara Cay Resort
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

7. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is AED 493
AED 675 total
includes taxes & fees
30 Nov - 1 Dec
Fisher Inn Resort & Marina
A resort with a pool, beach, and ocean view.

8. 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, (308 reviews)
  • cleanliness
    Sparkling pools welcome island adventurers to this oceanfront sanctuary with marina access and private beach lounging areas.
The price is AED 761
AED 1,125 total
includes taxes & fees
29 Nov - 30 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A poolside area with lounge chairs, a barbecue grill, and a view of the ocean.

9. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
The price is AED 702
AED 993 total
includes taxes & fees
15 Nov - 16 Nov
Pines & Palms Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.

10. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
The price is AED 418
AED 599 total
includes taxes & fees
9 Nov - 10 Nov
Drop Anchor
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.
View all properties

Choose what matters most at hotels with a pool in Islamorada

Breakfast included
Hot tub

Hotels with pools and free breakfast in Islamorada

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1810)
The price is AED 532
AED 805 total
includes taxes & fees
10 Nov - 11 Nov
Chesapeake Beach Resort
View all properties

Hotels with pools and hot tubs in Islamorada

A bathroom with a large bathtub, a view of the sea, and a pier with boats.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1511)
The price is AED 666
AED 1,018 total
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
View all properties

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, (1333)
The price is AED 599
AED 942 total
includes taxes & fees
15 Nov - 16 Nov
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.
View all properties

Top Islamorada Hotel Reviews

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.
Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor

10/10 Excellent

Best getaway in the Keys. Quiet, good vibes and friendly staff. Highly recommended.
United States
Audrey
Reviewed August 4, 2025
Kona Kai Resort and Gallery - Adults Only

Frequently Asked Questions

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'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.

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.