
Find Hotels with a Pool in Islamorada, FL
Check availability on Islamorada Hotels with a Pool
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Sep 17 - Sep 18Tomorrow
Sep 18 - Sep 19This weekend
Sep 18 - Sep 20Next weekend
Sep 25 - Sep 27Our 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.
$185 nightly
$208 total
Oct 18 - Oct 19
Total with taxes and fees




2. La Jolla Resort
La Jolla ResortMatecumbe
- Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
$89 nightly
$100 total
Oct 5 - Oct 6
Total with taxes and fees




3. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
$256 nightly
$288 total
Sep 27 - Sep 28
Total with taxes and fees




4. 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




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
$232 total
Sep 20 - Sep 21
Total with taxes and fees




6. 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.
$99 nightly
$112 total
Sep 30 - Oct 1
Total with taxes and fees




7. Ragged Edge Resort & Marina
Ragged Edge Resort & MarinaIslamorada
- Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
$99 nightly
$111 total
Sep 20 - Sep 21
Total with taxes and fees




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.
$139 nightly
$156 total
Sep 21 - Sep 22
Total with taxes and fees
View all properties
Hotels with pools and free breakfast in Islamorada
$185 nightly
$208 total
Oct 18 - Oct 19
Total with taxes and fees
$139 nightly
$156 total
Sep 21 - Sep 22
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
$264 nightly
$297 total
Sep 24 - Sep 25
Total with taxes and fees
$149 nightly
$168 total
Sep 20 - Sep 21
Total with taxes and fees
$164 nightly
$185 total
Sep 20 - Sep 21
Total with taxes and fees




Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
$117 nightly
$132 total
Sep 23 - Sep 24
Total with taxes and fees
$244 nightly
$275 total
Sep 20 - Sep 21
Total with taxes and fees




Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
$304 nightly
$342 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
$286 nightly
$322 total
Sep 28 - Sep 29
Total with taxes and fees
$99 nightly
$111 total
Oct 1 - Oct 2
Total with taxes and fees
Hotels with pools and hot tubs in Islamorada
$149 nightly
$168 total
Sep 20 - Sep 21
Total with taxes and fees
$186 nightly
$209 total
Sep 29 - Sep 30
Total with taxes and fees
$480 nightly
$539 total
Oct 18 - Oct 19
Total with taxes and fees




Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
$304 nightly
$342 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
$286 nightly
$322 total
Sep 28 - Sep 29
Total with taxes and fees




Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
$117 nightly
$132 total
Sep 23 - Sep 24
Total with taxes and fees
$148 nightly
$166 total
Sep 20 - Sep 21
Total with taxes and fees
$174 nightly
$196 total
Sep 21 - Sep 22
Total with taxes and fees
Top Islamorada Hotel Reviews
Chesapeake Beach Resort
10/10 Excellent
"Everything about the Chesapeake resort is perfect ,had the most incredible time ,will definitely return !!!"
La Jolla Resort
10/10 Excellent
"Great staff, very good location. Snorkeling by the dock is fun watching all the fish. One of the nicer, places in the keys"
Coconut Cove Resort and Marina
8/10 Good
"The location and property was well kept. Very nice pool and the room was very clean and worth the price. The welcoming was the best part, Crystal has a great attitude and very helpful with our questions both on property and in the town. We will come back"
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
10/10 Excellent
"We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area. The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere. Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!"
Hadley Resort and Marina
8/10 Good
"Great location and good rates for the 2 nights that we stayed. Staff was great and helpful. Closed to shops, cafe, and restaurants."
Drop Anchor
10/10 Excellent
"Great resort. Staff were helpful and the location is amazing"
Pines & Palms Resort
10/10 Excellent
"Loved staying here and would stay again. Staff were so friendly and nice - made you feel like you knew them for years."
The Caribbean Resort
10/10 Excellent
"Excellent place to stay!"
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