Find Hotels with a Pool in Islamorada, FL
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4 Sep - 6 SepOur top choices for Islamorada hotels with a pool
1. La Jolla Resort
La Jolla ResortMatecumbe
- Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
SAR 387
SAR 542 total
includes taxes & fees
31 Aug - 1 Sep
2. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
SAR 561
SAR 843 total
includes taxes & fees
31 Aug - 1 Sep
3. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
SAR 559
SAR 904 total
includes taxes & fees
9 Sep - 10 Sep
4. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
SAR 574
SAR 920 total
includes taxes & fees
2 Sep - 3 Sep
5. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
SAR 889
SAR 1,254 total
includes taxes & fees
2 Sep - 3 Sep
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.
SAR 376
SAR 483 total
includes taxes & fees
15 Sep - 16 Sep
7. 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.
SAR 428
SAR 650 total
includes taxes & fees
30 Aug - 31 Aug
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.
SAR 412
SAR 586 total
includes taxes & fees
21 Sep - 22 Sep
View all properties
Hotels with pools and free breakfast in Islamorada
SAR 561
SAR 843 total
includes taxes & fees
31 Aug - 1 Sep
SAR 543
SAR 610 total
includes taxes & fees
31 Aug - 1 Sep
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
SAR 658
SAR 1,015 total
includes taxes & fees
2 Sep - 3 Sep
SAR 412
SAR 586 total
includes taxes & fees
21 Sep - 22 Sep
SAR 412
SAR 586 total
includes taxes & fees
21 Sep - 22 Sep
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
SAR 927
SAR 1,250 total
includes taxes & fees
23 Sep - 24 Sep
SAR 706
SAR 942 total
includes taxes & fees
30 Aug - 31 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
SAR 921
SAR 1,243 total
includes taxes & fees
27 Sep - 28 Sep
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
SAR 351
SAR 514 total
includes taxes & fees
30 Aug - 31 Aug
SAR 544
SAR 612 total
includes taxes & fees
23 Sep - 24 Sep
Hotels with pools and hot tubs in Islamorada
SAR 559
SAR 904 total
includes taxes & fees
9 Sep - 10 Sep
SAR 543
SAR 610 total
includes taxes & fees
31 Aug - 1 Sep
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
SAR 351
SAR 514 total
includes taxes & fees
30 Aug - 31 Aug
SAR 448
SAR 609 total
includes taxes & fees
30 Aug - 31 Aug
SAR 1,325
SAR 1,724 total
includes taxes & fees
28 Aug - 29 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
SAR 921
SAR 1,243 total
includes taxes & fees
27 Sep - 28 Sep
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
SAR 927
SAR 1,250 total
includes taxes & fees
23 Sep - 24 Sep
SAR 581
SAR 654 total
includes taxes & fees
11 Sep - 12 Sep
SAR 274
SAR 1,104 total
includes taxes & fees
2 Sep - 3 Sep
SAR 507
SAR 1,312 total
includes taxes & fees
31 Aug - 1 Sep
4-star hotels with pools in Islamorada
SAR 574
SAR 920 total
includes taxes & fees
2 Sep - 3 Sep
SAR 889
SAR 1,254 total
includes taxes & fees
2 Sep - 3 Sep
SAR 560
SAR 905 total
includes taxes & fees
2 Sep - 3 Sep
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
SAR 658
SAR 1,015 total
includes taxes & fees
2 Sep - 3 Sep
SAR 1,325
SAR 1,724 total
includes taxes & fees
28 Aug - 29 Aug
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
SAR 927
SAR 1,250 total
includes taxes & fees
23 Sep - 24 Sep
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
SAR 921
SAR 1,243 total
includes taxes & fees
27 Sep - 28 Sep
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
8/10 Good
"We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after."
Cheeca Lodge & Spa
10/10 Excellent
"Trip was exceptional"
Casa Morada
8/10 Good
"The room was updated, clean, and comfortable. The bed and pillows were nice. The location was perfect for us. When it’s all completed it’s going to be a really cool spot for sunsets. Overall worth the money for a one nighter on our way home from the lower keys."
The Caribbean Resort
10/10 Excellent
"Excellent place to stay!"
Hadley Resort and Marina
10/10 Excellent
"Great spot for a vacation quiet clean spacious on the go breakfast. Also the ability to rent the boat while you’re there is also awesome. I would definitely reserve one beforehand. Other than that will be back again. I highly recommend this place."
La Siesta Resort & Villas
10/10 Excellent
"Wonderfully magical place that my wife and I enjoyed immensely! The beachfront bungalows were just perfect! Can't wait to see it again soon!"
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
10/10 Excellent
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Pines & Palms Resort
8/10 Good
"Lovely location, beautifully renovated, clean room, close to everything including great restaurants. If you want peace and quiet this is the spot for you. If your idea of the keys includes loud activities this is not for you. The small beach was not accessible due to rotting sargassum. You could not even spend much time at the pool due to the smell. Not the hotels fault obviously but affected our stay negatively."
Drop Anchor
8/10 Good
"Shower didn’t get super hot & not the best water pressure. Keep blinds closed in summer as the room got very hot and the a/c unit struggled to keep the room cool even at night. Could use a shade for the kitten window to help with this. Full length mirror in the room would’ve been nice as well. Overall nice property but a little older & can use some revamping"