Search Islamorada resorts with pools
Our top choices for a great stay
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! (8 reviews)
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Stay at this resort in Islamorada. Enjoy a fitness center, laundry facilities, and patios. Popular attractions Sunset Drive Beach and Anne's Beach are located ...
9.4/10 Exceptional! (3 reviews)
Cheeca Lodge & Spa
$264 nightly
The price is $297 total per night from Jun 3 to Jun 4
$297 total
Jun 3 - Jun 4
Total with taxes and fees
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,313 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
$319 nightly
The price is $359 total per night from Jun 29 to Jun 30
$359 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this 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! (202 reviews)
Matecumbe Resort
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 ...
9/10 Wonderful! (137 reviews)
Amara Cay Resort
$275 nightly
The price is $309 total per night from Jun 8 to Jun 9
$309 total
Jun 8 - Jun 9
Total with taxes and fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,287 reviews)
La Siesta Resort & Villas
$253 nightly
The price is $284 total per night from Jun 14 to Jun 15
$284 total
Jun 14 - Jun 15
Total with taxes and fees
Book a stay at this 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! (1,004 reviews)
On the water in Islamorada elevated detached unit!!!
Stay at this resort in Islamorada. Enjoy patios, cable/satellite TV service, and air conditioning. Popular attractions Sunset Drive Beach and Anne's Beach are ...
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.