Find Hotels with a Pool in Islamorada, FL
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Aug 28 - Aug 29Tomorrow
Aug 29 - Aug 30This weekend
Aug 28 - Aug 30Next weekend
Sep 4 - Sep 6Our 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.
￥15,122
￥21,495 total
includes taxes & fees
Sep 1 - Sep 2
2. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
￥22,106
￥33,833 total
includes taxes & fees
Sep 28 - Sep 29
3. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
￥23,731
￥38,344 total
includes taxes & fees
Sep 8 - Sep 9
4. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
￥21,438
￥35,772 total
includes taxes & fees
Aug 30 - Aug 31
5. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
￥38,085
￥53,595 total
includes taxes & fees
Sep 22 - Sep 23
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.
￥16,341
￥20,924 total
includes taxes & fees
Sep 8 - Sep 9
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.
￥17,851
￥27,250 total
includes taxes & fees
Aug 30 - Aug 31
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.
￥18,491
￥25,999 total
includes taxes & fees
Sep 21 - Sep 22
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Hotels with pools and free breakfast in Islamorada
￥22,106
￥33,833 total
includes taxes & fees
Sep 28 - Sep 29
￥22,083
￥24,843 total
includes taxes & fees
Sep 28 - Sep 29
￥18,491
￥25,999 total
includes taxes & fees
Sep 21 - Sep 22
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
￥27,904
￥43,038 total
includes taxes & fees
Sep 7 - Sep 8
￥18,491
￥25,999 total
includes taxes & fees
Sep 20 - Sep 21
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
￥39,340
￥53,038 total
includes taxes & fees
Sep 20 - Sep 21
￥29,958
￥39,974 total
includes taxes & fees
Aug 30 - Aug 31
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
￥37,765
￥51,272 total
includes taxes & fees
Sep 28 - Sep 29
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
￥14,916
￥21,833 total
includes taxes & fees
Aug 30 - Aug 31
￥23,094
￥25,982 total
includes taxes & fees
Aug 31 - Sep 1
Hotels with pools and hot tubs in Islamorada
￥23,731
￥38,344 total
includes taxes & fees
Sep 8 - Sep 9
￥22,083
￥24,843 total
includes taxes & fees
Sep 28 - Sep 29
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
￥14,916
￥21,833 total
includes taxes & fees
Aug 30 - Aug 31
￥18,985
￥25,838 total
includes taxes & fees
Aug 31 - Sep 1
￥57,337
￥74,430 total
includes taxes & fees
Aug 29 - Aug 30
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
￥37,765
￥51,272 total
includes taxes & fees
Sep 28 - Sep 29
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
￥39,340
￥53,038 total
includes taxes & fees
Sep 20 - Sep 21
￥24,938
￥28,055 total
includes taxes & fees
Sep 11 - Sep 12
￥12,142
￥47,603 total
includes taxes & fees
Sep 2 - Sep 3
￥21,501
￥55,645 total
includes taxes & fees
Aug 31 - Sep 1
4-star hotels with pools in Islamorada
￥21,438
￥35,772 total
includes taxes & fees
Aug 30 - Aug 31
￥38,085
￥53,595 total
includes taxes & fees
Sep 22 - Sep 23
￥21,394
￥35,715 total
includes taxes & fees
Sep 3 - Sep 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
￥27,904
￥43,038 total
includes taxes & fees
Sep 7 - Sep 8
￥57,337
￥74,430 total
includes taxes & fees
Aug 29 - Aug 30
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
￥39,340
￥53,038 total
includes taxes & fees
Sep 20 - Sep 21
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
￥37,765
￥51,272 total
includes taxes & fees
Sep 28 - Sep 29
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."
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."
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"