Search Islamorada resorts with pools

Our top choices for a great stay

Keys Villa

Keys Villa

Stay at this resort in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Sunset Drive Beach and Anne's Beach are located ...
10/10 Exceptional! (6 reviews)
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Keys Villa
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
The price is CA $213 per night from Aug 17 to Aug 18
CA $213
CA $333 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,143 reviews)
Cheeca Lodge & Spa
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

3.5 out of 5
The price is CA $269 per night from Sep 1 to Sep 2
CA $269
CA $394 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this 3.5-star beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (57 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

Stay at this resort in Islamorada. Enjoy laundry facilities, patios, and air conditioning. Popular attractions Sunset Drive Beach and Anne's Beach are located ...
9/10 Wonderful! (2 reviews)
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2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Amara Cay Resort

Amara Cay Resort

4 out of 5
The price is CA $232 per night from Sep 1 to Sep 2
CA $232
CA $353 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,231 reviews)
Amara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
The price is CA $196 per night from Sep 16 to Sep 17
CA $196
CA $313 total
Sep 16 - Sep 17
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
8.6/10 Excellent! (1,001 reviews)
La Siesta Resort & Villas
Matecumbe Resort

Matecumbe Resort

2 out of 5
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, free parking, and a private beach. Popular attractions Robbie’s of Islamorada and Indian Key ...
8.6/10 Excellent! (66 reviews)
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Matecumbe Resort
Beautiful oceanfront resort located at mile marker 73.8

Beautiful oceanfront resort located at mile marker 73.8

Stay at this resort in Islamorada. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Anne's Beach and Sunset Drive Beach ...
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Beautiful oceanfront resort located at mile marker 73.8
JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub

JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub

Stay at this resort in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Sunset Drive Beach and Anne's Beach are located ...
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JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub
On the water in Islamorada elevated detached unit!!!

On the water in Islamorada elevated detached unit!!!

Stay at this resort in Islamorada. Enjoy cable/satellite TV service, air conditioning, and an outdoor pool. Popular attractions Sunset Drive Beach and Anne's ...
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On the water in Islamorada elevated detached unit!!!
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.