
Find Hotels with a Pool in Islamorada, FL
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Check availability on Islamorada Hotels with a Pool
Tonight
Sep 26 - Sep 27Tomorrow
Sep 27 - Sep 28Next weekend
Oct 2 - Oct 4In two weeks
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.
$188 nightly
$212 total
Sep 30 - Oct 1
Total with taxes and fees




2. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
$186 nightly
$209 total
Sep 29 - Sep 30
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.
$105 nightly
$118 total
Sep 29 - Sep 30
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
Sep 29 - Sep 30
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.
$206 nightly
$231 total
Oct 4 - Oct 5
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 28 - Sep 29
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.
$282 nightly
$318 total
Oct 26 - Oct 27
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
Oct 6 - Oct 7
Total with taxes and fees
View all properties
Hotels with pools and free breakfast in Islamorada
$188 nightly
$212 total
Sep 30 - Oct 1
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 6 - Oct 7
Total with taxes and fees
$133 nightly
$149 total
Oct 6 - Oct 7
Total with taxes and fees
$156 nightly
$175 total
Sep 28 - Sep 29
Total with taxes and fees




Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
$312 nightly
$351 total
Oct 11 - Oct 12
Total with taxes and fees
$147 nightly
$166 total
Sep 28 - Sep 29
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 29 - Sep 30
Total with taxes and fees
$244 nightly
$275 total
Sep 27 - Sep 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
$85 nightly
$96 total
Sep 30 - Oct 1
Total with taxes and fees
Hotels with pools and hot tubs in Islamorada
$133 nightly
$149 total
Oct 6 - Oct 7
Total with taxes and fees
$186 nightly
$209 total
Sep 29 - Sep 30
Total with taxes and fees




Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
$312 nightly
$351 total
Oct 11 - Oct 12
Total with taxes and fees
$504 nightly
$566 total
Oct 1 - Oct 2
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 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
$124 nightly
$139 total
Oct 1 - Oct 2
Total with taxes and fees
$152 nightly
$171 total
Sep 28 - Sep 29
Total with taxes and fees
Top Islamorada Hotel Reviews
Islander Resort
8/10 Good
"I liked the fact that our rear outside seating area was quite private because of the trees and bushes growing around the property. Very peaceful and also just a couple of minutes walk from the sea."
Chesapeake Beach Resort
8/10 Good
"I liked the breakfast. One pool was being worked on and the pool workers helped themselves to the free breakfast. Some of them stood in the coffee and drink area and ate their free breakfast. The tree trimmers took up some of relaxing areas and they were noisy. The cleaning staff and the front desk staff were very good. The breakfast cook was friendly. The spa was hot but no jet action. We probably won’t be coming back. Thanks"
Casa Morada
10/10 Excellent
"always a favorite!"
La Jolla Resort
8/10 Good
"Loved the amenities"
Drop Anchor
10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Fisher Inn Resort & Marina
10/10 Excellent
"This place was the best place to stay I've ever been ever it is wonderful there's nothing not to like about this place the ocean the pool the people the place everybody's so nice and accommodating they will do anything they can to make sure you're happy it's paradise in paradise I would suggest to stay at this place anytime it would be a mistake not to"
Coconut Cove Resort and Marina
10/10 Excellent
"Excellent stay! Love this place and will definitely be back!"
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