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Featured Islamorada Family Hotels
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
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 ...
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
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 ...
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
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 ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
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 ...
Conch On Inn Motel
103 Caloosa Street Tavernier FL
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Old Road Gallery and Florida Keys Dive Center are ...
The Caribbean Resort
117 Carroll St Islamorada FL
Book a stay at this family-friendly hotel in Islamorada. Enjoy a marina, free bicycles on site, and daily housekeeping. Popular attractions Keys History & Discovery ...
Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 3 restaurants. Popular attractions Hurricane Monument and MoradaWay Arts & ...
Sands of Islamorada
80051 Overseas Highway Islamorada FL
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument ...
Creekside Inn
90611 Old Highway Tavernier FL
Fully refundableReserve now, pay when you stay
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
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.
Hotels with Pools in Islamorada
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
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! (1,273 reviews)
All issues were addressed quickly and professionally. Room was large/ spacious. Views were gorgeous. Tiki bar staff was awesome.
Reviewed on Jan 4, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,006 reviews)
Clean room and resort. So much to do. Absolutely beautiful
Reviewed on Dec 28, 2025
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
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! (1,003 reviews)
What a great place to stay, beautiful resort with beautiful surroundings.
Reviewed on Jan 2, 2026
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.
Hotels With Connecting Rooms in Islamorada
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
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 ...
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
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 ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
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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Hotels by Star Rating
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- Hotels with a Pool in Islamorada
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Other Accommodation Types
Islamorada Neighborhoods
Top Points of Interests in Islamorada
- Hotels near Anne's Beach
- Hotels near Bud n' Mary's Dive Center
- Hotels near Florida Keys Brewing Co.
- Hotels near Founders Park
- Hotels near Islamorada County Park
- Hotels near Windley Key Fossil Reef Geological State Park
- Hotels near Robbie’s of Islamorada
- Hotels near Islamorada Brewery & Distillery
- Hotels near History of Diving Museum
- Hotels near Sunset Drive Beach
- Hotels near Hurricane Monument
- Hotels near Rain Barrel Village
- Hotels near Keys History & Discovery Center
- Hotels near MoradaWay Arts & Cultural District
- Hotels near Matecumbe United Methodist Church
- Hotels near Everglades National Park
- Hotels near John Pennekamp Coral Reef State Park
- Hotels near Baker's Cay Resort Beach
- Hotels near Jimmy Johnson's Big Chill
- Hotels near Florida Keys Visitor Center - Key Largo
Cities near Islamorada
- Key Largo Hotels (16.51 mi)
- Marathon Hotels (31.76 mi)
- Florida Keys Hotels (34.7 mi)
- Tavernier Hotels (9.28 mi)
- Key Colony Beach Hotels (28.23 mi)
- Long Key Hotels (13.9 mi)
- South Florida Hotels (108.84 mi)
- Duck Key Hotels (20.71 mi)
- Grassy Key Hotels (23.2 mi)
- Layton Hotels (13.54 mi)
- Southeastern United States Hotels (582.55 mi)
- Conch Key Hotels (18.84 mi)
- Gulf of Mexico Hotels (607.73 mi)
- The South Hotels (807.77 mi)
- Lignumvitae Key Botanical State Park Hotels (4.47 mi)