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! (7 reviews)
Cheeca Lodge & Spa
The price is CA $674 per night from Jan 3 to Jan 4
CA $674
CA $860 total
Jan 3 - Jan 4, 2026
includes taxes & 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! (1,267 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
The price is CA $409 per night from Jan 4 to Jan 5
CA $409
CA $551 total
Jan 4 - Jan 5, 2026
includes taxes & 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! (115 reviews)
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)
Amara Cay Resort
The price is CA $302 per night from Jan 4 to Jan 5
CA $302
CA $432 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy a private beach, 3 bars/lounges, and breakfast (surcharge). Our guests praise the pool and the helpful ...
8.8/10 Excellent! (1,265 reviews)
Matecumbe Resort
The price is CA $219 per night from Jan 13 to Jan 14
CA $219
CA $247 total
Jan 13 - Jan 14, 2026
includes taxes & fees
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 ...
8.8/10 Excellent! (83 reviews)
La Siesta Resort & Villas
The price is CA $273 per night from Jan 11 to Jan 12
CA $273
CA $399 total
Jan 11 - Jan 12, 2026
includes taxes & 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! (1,001 reviews)
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 ...
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 ...
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.
