
Find Hotels with a Pool in Islamorada, FL
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Check availability on Islamorada Hotels with a Pool
Tonight
Sep 28 - Sep 29Tomorrow
Sep 29 - Sep 30This weekend
Oct 2 - Oct 4Next weekend
Oct 9 - Oct 11Our 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.
$186 nightly
$209 total
Oct 6 - Oct 7
Total with taxes and fees




2. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
$193 nightly
$217 total
Sep 30 - Oct 1
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.
$112 nightly
$126 total
Oct 6 - Oct 7
Total with taxes and fees




4. 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.
$107 nightly
$120 total
Oct 4 - Oct 5
Total with taxes and fees




5. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
$209 nightly
$235 total
Sep 30 - Oct 1
Total with taxes and fees




6. 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.
$156 nightly
$175 total
Sep 29 - Sep 30
Total with taxes and fees




7. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
$309 nightly
$347 total
Sep 30 - Oct 1
Total with taxes and fees




8. Lime Tree Bay Resort
Lime Tree Bay ResortLong Key
- A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
$148 nightly
$167 total
Sep 30 - Oct 1
Total with taxes and fees
View all properties
Hotels with pools and free breakfast in Islamorada
$186 nightly
$209 total
Oct 6 - Oct 7
Total with taxes and fees
$133 nightly
$149 total
Oct 27 - Oct 28
Total with taxes and fees
$156 nightly
$175 total
Sep 29 - Sep 30
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
Oct 13 - Oct 14
Total with taxes and fees
$164 nightly
$185 total
Sep 29 - Sep 30
Total with taxes and fees




Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
$126 nightly
$142 total
Oct 4 - Oct 5
Total with taxes and fees
$244 nightly
$275 total
Oct 5 - Oct 6
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
$311 nightly
$350 total
Sep 30 - Oct 1
Total with taxes and fees




Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
$312 nightly
$351 total
Oct 12 - Oct 13
Total with taxes and fees
$85 nightly
$96 total
Sep 30 - Oct 1
Total with taxes and fees
Hotels with pools and hot tubs in Islamorada
$193 nightly
$217 total
Sep 30 - Oct 1
Total with taxes and fees
$133 nightly
$149 total
Oct 27 - Oct 28
Total with taxes and fees




Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
$126 nightly
$142 total
Oct 4 - Oct 5
Total with taxes and fees
$186 nightly
$209 total
Sep 29 - Sep 30
Total with taxes and fees
$124 nightly
$139 total
Sep 29 - Sep 30
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
$311 nightly
$350 total
Sep 30 - Oct 1
Total with taxes and fees
$514 nightly
$577 total
Sep 30 - Oct 1
Total with taxes and fees




Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
$312 nightly
$351 total
Oct 12 - Oct 13
Total with taxes and fees
$267 nightly
$297 total
Oct 4 - Oct 5
Total with taxes and fees




Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQTavernier
$310 nightly
$346 total
Sep 29 - Sep 30
Total with taxes and fees
Top Islamorada Hotel Reviews
Chesapeake Beach Resort
10/10 Excellent
"Very beautiful place. Besides breakfast but we didn't stay hungry. Beside that, everything was perfect"
Cheeca Lodge & Spa
10/10 Excellent
"We booked this last minute traveling through the keys on our way to Key West. It was a fantastic place to stay. The staff were so friendly and helpful and the property was beautiful. Highly recommend. I hope we can come back and stay longer next time."
Amara Cay Resort
10/10 Excellent
"All was nice!!"
La Jolla Resort
8/10 Good
"Old buildings but the room was very comfortable. Bring an eye mask as there are no curtains and it gets very bright. There are a lot of cool things to do on the property including fish from the dock (gear and bait are available and free!), kayaking, paddle boarding, corn hole, and shuffle board. The resident cat Felix is adorable. It stays pretty quiet and is a peaceful escape."
Casa Morada
10/10 Excellent
"always a favorite!"
Drop Anchor
10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
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