Find Hotels with a Pool in Islamorada, FL
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Sep 7 - Sep 8Tomorrow
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Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Our top choices for Islamorada hotels with a pool
1. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
NT$3,762
NT$6,007 total
includes taxes & fees
Sep 13 - Sep 14
2. Pines & Palms Resort
Pines & Palms ResortMatecumbe
- Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
NT$3,702
NT$5,909 total
includes taxes & fees
Sep 9 - Sep 10
3. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
NT$4,714
NT$7,618 total
includes taxes & fees
Sep 9 - Sep 10
4. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
NT$4,877
NT$7,793 total
includes taxes & fees
Sep 14 - Sep 15
5. Breezy Palms Resort
Breezy Palms ResortMatecumbe
- Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
NT$2,518
NT$3,337 total
includes taxes & fees
Sep 9 - Sep 10
6. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
NT$6,176
NT$9,077 total
includes taxes & fees
Sep 14 - Sep 15
7. Ragged Edge Resort & Marina
Ragged Edge Resort & MarinaIslamorada
- Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
NT$2,211
NT$2,487 total
includes taxes & fees
Sep 13 - Sep 14
8. Fisher Inn Resort & Marina
Fisher Inn Resort & MarinaIslamorada
- Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
NT$3,738
NT$5,238 total
includes taxes & fees
Sep 21 - Sep 22
View all properties
Hotels with pools and free breakfast in Islamorada
NT$3,762
NT$6,007 total
includes taxes & fees
Sep 13 - Sep 14
NT$3,738
NT$5,238 total
includes taxes & fees
Sep 21 - Sep 22
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
NT$5,780
NT$8,809 total
includes taxes & fees
Sep 14 - Sep 15
NT$4,701
NT$5,288 total
includes taxes & fees
Sep 9 - Sep 10
NT$4,276
NT$5,843 total
includes taxes & fees
Sep 9 - Sep 10
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
NT$3,095
NT$4,482 total
includes taxes & fees
Sep 14 - Sep 15
NT$5,951
NT$7,941 total
includes taxes & fees
Sep 9 - Sep 10
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
NT$8,045
NT$10,790 total
includes taxes & fees
Sep 30 - Oct 1
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
NT$7,476
NT$10,150 total
includes taxes & fees
Sep 30 - Oct 1
NT$2,824
NT$3,177 total
includes taxes & fees
Sep 9 - Sep 10
Hotels with pools and hot tubs in Islamorada
NT$4,714
NT$7,618 total
includes taxes & fees
Sep 9 - Sep 10
NT$4,701
NT$5,288 total
includes taxes & fees
Sep 9 - Sep 10
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
NT$3,095
NT$4,482 total
includes taxes & fees
Sep 14 - Sep 15
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
NT$8,045
NT$10,790 total
includes taxes & fees
Sep 30 - Oct 1
NT$12,814
NT$16,416 total
includes taxes & fees
Sep 9 - Sep 10
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
NT$7,476
NT$10,150 total
includes taxes & fees
Sep 30 - Oct 1
NT$4,243
NT$5,663 total
includes taxes & fees
Sep 9 - Sep 10
NT$4,799
NT$5,398 total
includes taxes & fees
Sep 20 - Sep 21
4-star hotels with pools in Islamorada
NT$6,176
NT$9,077 total
includes taxes & fees
Sep 14 - Sep 15
NT$4,877
NT$7,793 total
includes taxes & fees
Sep 14 - Sep 15
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
NT$5,780
NT$8,809 total
includes taxes & fees
Sep 14 - Sep 15
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
NT$8,045
NT$10,790 total
includes taxes & fees
Sep 30 - Oct 1
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
NT$7,476
NT$10,150 total
includes taxes & fees
Sep 30 - Oct 1
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 propertiesTop Islamorada Hotel Reviews
Cheeca Lodge & Spa
10/10 Excellent
"Absolutely amazing experience at Cheeca Lodge & Spa! From the moment we arrived, the service was welcoming, professional, and attentive. The resort is beautiful, peaceful, and perfectly captures the tropical atmosphere of the Florida Keys. The grounds are immaculate, the ocean views are breathtaking, and the entire property has a relaxing yet luxurious feel. The food and drinks were excellent, and the staff consistently went above and beyond to make our stay special. Watching the sunset and enjoying the beautiful surroundings made the experience even more memorable. 🌴🌅 Cheeca is the perfect place for a relaxing getaway with family or a romantic escape. We truly enjoyed every moment and will definitely be coming back. Highly recommended!"
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
10/10 Excellent
"Todo muy bueno súper limpio la comida muy rica me encantó"
Pines & Palms Resort
10/10 Excellent
"After multiple visits to Islamorada this is now our new place to stay whenever we visit. Great location, beautiful property and incredibly friendly staff!!"
Fisher Inn Resort & Marina
8/10 Good
"Everything was excellent, except in the room with our extra bed sofa bed we didn’t have any pillows or blankets to accommodate the other two people, and there was no more towels in the pool clean otherwise everything was good. Staff was excellent and friendly."
Islander Resort
10/10 Excellent
"Everything is super great beside Beach If you looking to swim in the ocean not best pick"
Breezy Palms Resort
10/10 Excellent
"El lugar muy bueno agradable y limpio!!! Con condiciones para pasar una vacaciones Repetiríamos"
La Jolla Resort
10/10 Excellent
"Loved this place! driving in I wasn’t too sure but when we open the door to our King suite absolutely stunning clean smelled amazing and walk right up to the water. You can paddleboard kayak. We loved our stay."
Coconut Cove Resort and Marina
10/10 Excellent
"Amazing customer service"
La Siesta Resort & Villas
10/10 Excellent
"Maravillosa estancia, nos encantó todo ❤️"
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