Islamorada Hotel with Pool
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7 Aug - 8 AugTomorrow
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7 Aug - 9 AugNext weekend
14 Aug - 16 AugOur 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.
HK$1,185
HK$1,774 total
includes taxes & fees
11 Aug - 12 Aug
2. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
HK$1,326
HK$2,065 total
includes taxes & fees
10 Aug - 11 Aug
3. La Jolla Resort
La Jolla ResortMatecumbe
- Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
HK$801
HK$1,122 total
includes taxes & fees
12 Aug - 13 Aug
4. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
HK$1,318
HK$2,057 total
includes taxes & fees
19 Aug - 20 Aug
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.
HK$732
HK$1,231 total
includes taxes & fees
3 Sept - 4 Sept
6. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
HK$1,836
HK$2,595 total
includes taxes & fees
31 Aug - 1 Sept
7. 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.
HK$860
HK$1,223 total
includes taxes & fees
31 Aug - 1 Sept
8. Pines & Palms Resort
Pines & Palms ResortMatecumbe
- Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
HK$1,374
HK$1,979 total
includes taxes & fees
30 Aug - 31 Aug
View all properties
Hotels with pools and free breakfast in Islamorada
HK$1,185
HK$1,774 total
includes taxes & fees
11 Aug - 12 Aug
HK$860
HK$1,223 total
includes taxes & fees
31 Aug - 1 Sept
HK$860
HK$1,224 total
includes taxes & fees
7 Sept - 8 Sept
HK$1,169
HK$1,315 total
includes taxes & fees
30 Aug - 31 Aug
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
HK$1,625
HK$2,402 total
includes taxes & fees
17 Aug - 18 Aug
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
HK$769
HK$1,114 total
includes taxes & fees
2 Sept - 3 Sept
HK$1,137
HK$1,280 total
includes taxes & fees
1 Sept - 2 Sept
HK$1,476
HK$1,969 total
includes taxes & fees
9 Aug - 10 Aug
HK$1,294
HK$1,456 total
includes taxes & fees
26 Aug - 27 Aug
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
HK$1,875
HK$2,542 total
includes taxes & fees
30 Aug - 31 Aug
Hotels with pools and hot tubs in Islamorada
HK$1,326
HK$2,065 total
includes taxes & fees
10 Aug - 11 Aug
HK$1,169
HK$1,315 total
includes taxes & fees
30 Aug - 31 Aug
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
HK$769
HK$1,114 total
includes taxes & fees
2 Sept - 3 Sept
HK$1,186
HK$1,555 total
includes taxes & fees
9 Aug - 10 Aug
HK$2,510
HK$3,256 total
includes taxes & fees
19 Aug - 20 Aug
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
HK$1,875
HK$2,542 total
includes taxes & fees
30 Aug - 31 Aug
HK$713
HK$2,449 total
includes taxes & fees
30 Aug - 31 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
HK$1,923
HK$2,596 total
includes taxes & fees
17 Aug - 18 Aug
HK$1,334
HK$1,501 total
includes taxes & fees
19 Aug - 20 Aug
HK$1,059
HK$2,701 total
includes taxes & fees
9 Aug - 10 Aug
4-star hotels with pools in Islamorada
HK$1,318
HK$2,057 total
includes taxes & fees
19 Aug - 20 Aug
HK$1,836
HK$2,595 total
includes taxes & fees
31 Aug - 1 Sept
HK$1,212
HK$1,938 total
includes taxes & fees
13 Aug - 14 Aug
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
HK$1,625
HK$2,402 total
includes taxes & fees
17 Aug - 18 Aug
HK$2,510
HK$3,256 total
includes taxes & fees
19 Aug - 20 Aug
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
HK$1,875
HK$2,542 total
includes taxes & fees
30 Aug - 31 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
HK$1,923
HK$2,596 total
includes taxes & fees
17 Aug - 18 Aug
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
Chesapeake Beach Resort
10/10 Excellent
"Service was great, room clean and spacious. Definitely will be coming back"
Cheeca Lodge & Spa
8/10 Good
"My family had a wonderful time. We took advantage of the bikes, fishing, kayaks, kids club, etc. Will def be coming back!"
Fisher Inn Resort & Marina
10/10 Excellent
"Lo único malo q tenía muchas algas en el lado de la marina no pesqué nada pero la pasé bien"
Coconut Cove Resort and Marina
10/10 Excellent
"Wow! I stayed there for a week and I really felt like I was in my little slice of heaven! The resort is decorated beautifully. The room definitely has the Florida keys vibe and the staff were so awesome. I would have loved to stay there forever. I can't wait to go back!!!"
La Jolla Resort
10/10 Excellent
"LaJolla was great with so many amenities. We really enjoyed our stay here."
Pines & Palms Resort
10/10 Excellent
"El lugar es excelente ,bien limpio y renovado"
La Siesta Resort & Villas
10/10 Excellent
"The check in staff was amazing and helpful. There was a lot of included things to do that were really nice and easy to access. There was a strong fish smell, but that was likely because people catch/clean their fish at the dock and there was a bit of sea grass along the shore that likely contributed. We'd stay there again for sure!"
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