
Find Hotels with a Pool in Islamorada, FL
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Check availability on Islamorada Hotels with a Pool
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Aug 7 - Aug 8Tomorrow
Aug 8 - Aug 9This weekend
Aug 7 - Aug 9Next weekend
Aug 14 - Aug 16Our 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.
$197 nightly
$221 total
Aug 11 - Aug 12
Total with taxes and fees




2. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
$202 nightly
$227 total
Aug 10 - Aug 11
Total with taxes and fees




3. La Jolla Resort
La Jolla ResortMatecumbe
- Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
$127 nightly
$143 total
Aug 12 - Aug 13
Total with taxes and fees




4. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
$221 nightly
$248 total
Aug 11 - Aug 12
Total with taxes and fees




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.
$138 nightly
$155 total
Aug 10 - Aug 11
Total with taxes and fees




6. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
$294 nightly
$331 total
Aug 31 - Sep 1
Total with taxes and fees




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.
$136 nightly
$153 total
Aug 27 - Aug 28
Total with taxes and fees




8. Pines & Palms Resort
Pines & Palms ResortMatecumbe
- Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
$220 nightly
$248 total
Aug 30 - Aug 31
Total with taxes and fees
View all properties
Hotels with pools and free breakfast in Islamorada
$197 nightly
$221 total
Aug 11 - Aug 12
Total with taxes and fees
$136 nightly
$153 total
Aug 27 - Aug 28
Total with taxes and fees
$138 nightly
$155 total
Aug 12 - Aug 13
Total with taxes and fees
$146 nightly
$164 total
Aug 30 - Aug 31
Total with taxes and fees




Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
$272 nightly
$306 total
Aug 17 - Aug 18
Total with taxes and fees




Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
$116 nightly
$131 total
Sep 7 - Sep 8
Total with taxes and fees
$145 nightly
$163 total
Aug 30 - Aug 31
Total with taxes and fees
$244 nightly
$275 total
Aug 9 - Aug 10
Total with taxes and fees
$165 nightly
$186 total
Aug 26 - Aug 27
Total with taxes and fees




Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
$288 nightly
$324 total
Aug 30 - Aug 31
Total with taxes and fees
Hotels with pools and hot tubs in Islamorada
$202 nightly
$227 total
Aug 10 - Aug 11
Total with taxes and fees
$146 nightly
$164 total
Aug 30 - Aug 31
Total with taxes and fees




Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
$116 nightly
$131 total
Sep 7 - Sep 8
Total with taxes and fees
$176 nightly
$198 total
Aug 9 - Aug 10
Total with taxes and fees
$361 nightly
$406 total
Aug 17 - Aug 18
Total with taxes and fees




Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
$288 nightly
$324 total
Aug 30 - Aug 31
Total with taxes and fees
$281 nightly
$312 total
Aug 30 - Aug 31
Total with taxes and fees




Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
$294 nightly
$331 total
Aug 17 - Aug 18
Total with taxes and fees
$162 nightly
$182 total
Aug 17 - Aug 18
Total with taxes and fees
$310 nightly
$344 total
Aug 9 - Aug 10
Total with taxes and fees
Top Islamorada Hotel Reviews
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!"
Islander Resort
10/10 Excellent
"We loved this …the room was nice and large and a huge patio…we loved the Puttputt golf and bocie ball…lovely place across the street to see the sunset too"
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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