Hotels with Swimming Pool in Islamorada, Florida
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Aug 15 - Aug 16Tomorrow
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Aug 21 - Aug 23In two weeks
Aug 28 - Aug 30Our 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.
P9,266
P13,875 total
includes taxes & fees
Aug 26 - Aug 27
2. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
P9,156
P14,794 total
includes taxes & fees
Aug 18 - Aug 19
3. La Jolla Resort
La Jolla ResortMatecumbe
- Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
P6,833
P9,416 total
includes taxes & fees
Aug 25 - Aug 26
4. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
P10,311
P16,086 total
includes taxes & fees
Aug 18 - Aug 19
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.
P6,294
P8,060 total
includes taxes & fees
Sep 2 - Sep 3
6. Drop Anchor
Drop AnchorIslamorada
- Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
P5,828
P8,707 total
includes taxes & fees
Aug 16 - Aug 17
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.
P6,217
P8,999 total
includes taxes & fees
Sep 1 - Sep 2
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.
P6,887
P10,513 total
includes taxes & fees
Aug 18 - Aug 19
View all properties
Hotels with pools and free breakfast in Islamorada
P9,266
P13,875 total
includes taxes & fees
Aug 26 - Aug 27
P6,217
P8,999 total
includes taxes & fees
Sep 1 - Sep 2
P6,726
P9,569 total
includes taxes & fees
Sep 10 - Sep 11
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
P12,732
P18,818 total
includes taxes & fees
Sep 7 - Sep 8
P9,140
P10,283 total
includes taxes & fees
Sep 13 - Sep 14
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
P6,018
P8,715 total
includes taxes & fees
Sep 10 - Sep 11
P8,895
P10,007 total
includes taxes & fees
Sep 13 - Sep 14
P11,559
P15,423 total
includes taxes & fees
Aug 16 - Aug 17
P10,122
P11,387 total
includes taxes & fees
Sep 13 - Sep 14
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
P14,661
P19,876 total
includes taxes & fees
Aug 31 - Sep 1
Hotels with pools and hot tubs in Islamorada
P9,156
P14,794 total
includes taxes & fees
Aug 18 - Aug 19
P9,140
P10,283 total
includes taxes & fees
Sep 13 - Sep 14
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
P14,661
P19,876 total
includes taxes & fees
Aug 31 - Sep 1
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
P14,538
P19,737 total
includes taxes & fees
Aug 24 - Aug 25
P22,084
P28,668 total
includes taxes & fees
Sep 13 - Sep 14
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
P6,018
P8,715 total
includes taxes & fees
Sep 10 - Sep 11
P9,291
P12,181 total
includes taxes & fees
Aug 16 - Aug 17
P10,435
P11,739 total
includes taxes & fees
Aug 28 - Aug 29
4-star hotels with pools in Islamorada
P10,311
P16,086 total
includes taxes & fees
Aug 18 - Aug 19
P9,482
P15,154 total
includes taxes & fees
Aug 18 - Aug 19
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
P12,732
P18,818 total
includes taxes & fees
Sep 7 - Sep 8
P14,232
P20,152 total
includes taxes & fees
Sep 13 - Sep 14
P22,084
P28,668 total
includes taxes & fees
Sep 13 - Sep 14
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
P14,661
P19,876 total
includes taxes & fees
Aug 31 - Sep 1
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
P14,538
P19,737 total
includes taxes & fees
Aug 24 - Aug 25
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
"10/10 recommend! We will be back again! We love coming here and bringing the boat. Staff is great and properly/rooms are so clean."
Amara Cay Resort
10/10 Excellent
"Always a good time!"
Breezy Palms Resort
10/10 Excellent
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
Drop Anchor
10/10 Excellent
"We were only there two nights so we didn’t have much interaction with the staff, but it was well kept and convenient for our needs as a family."
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
10/10 Excellent
"Stayed in build 7 and it had a great view restaurant was good the bars where nice and most of all I booked a fishing trip with Whiskey Throttle guide service and Sean put me on a dinosaur of a tarpon and boy was it a beast. If the fishing is slow grab Whiskey Throttle for a great water adventures."
Hadley Resort and Marina
8/10 Good
"For the price, this place is great!!! Very clean, spacious rooms… free breakfast! Staff very nice. Great location… everything is 5mins away! Would return here"
Casa Morada
10/10 Excellent
"It's a beautiful property! A hidden treasure in Islamorada : )"
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."