Find Hotels with a Pool in Islamorada, FL
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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.
NT$3,271
NT$4,572 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.
NT$4,788
NT$7,169 total
includes taxes & fees
Aug 30 - Aug 31
3. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
NT$4,723
NT$7,631 total
includes taxes & fees
Sep 2 - Sep 3
4. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
NT$4,686
NT$7,590 total
includes taxes & fees
Sep 2 - Sep 3
5. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
NT$7,734
NT$10,841 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.
NT$3,252
NT$4,164 total
includes taxes & fees
Sep 2 - Sep 3
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.
NT$3,553
NT$5,423 total
includes taxes & fees
Aug 31 - Sep 1
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.
NT$3,680
NT$5,174 total
includes taxes & fees
Sep 21 - Sep 22
View all properties
Hotels with pools and free breakfast in Islamorada
NT$4,788
NT$7,169 total
includes taxes & fees
Aug 30 - Aug 31
NT$4,723
NT$5,313 total
includes taxes & fees
Aug 30 - Aug 31
NT$3,680
NT$5,174 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
NT$5,553
NT$8,566 total
includes taxes & fees
Sep 7 - Sep 8
NT$3,680
NT$5,174 total
includes taxes & fees
Sep 20 - Sep 21
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
NT$7,829
NT$10,556 total
includes taxes & fees
Sep 20 - Sep 21
NT$5,962
NT$7,956 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
NT$7,512
NT$10,198 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
NT$2,967
NT$4,343 total
includes taxes & fees
Aug 30 - Aug 31
NT$4,596
NT$5,171 total
includes taxes & fees
Aug 30 - Aug 31
Hotels with pools and hot tubs in Islamorada
NT$4,723
NT$7,631 total
includes taxes & fees
Sep 2 - Sep 3
NT$4,723
NT$5,313 total
includes taxes & fees
Aug 30 - Aug 31
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
NT$2,967
NT$4,343 total
includes taxes & fees
Aug 30 - Aug 31
NT$3,778
NT$5,142 total
includes taxes & fees
Aug 30 - Aug 31
NT$11,411
NT$14,813 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
NT$7,512
NT$10,198 total
includes taxes & fees
Sep 28 - Sep 29
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
NT$7,829
NT$10,556 total
includes taxes & fees
Sep 20 - Sep 21
NT$5,392
NT$6,066 total
includes taxes & fees
Sep 11 - Sep 12
4-star hotels with pools in Islamorada
NT$4,686
NT$7,590 total
includes taxes & fees
Sep 2 - Sep 3
NT$7,734
NT$10,841 total
includes taxes & fees
Sep 22 - Sep 23
NT$4,258
NT$7,108 total
includes taxes & fees
Aug 31 - Sep 1
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
NT$5,553
NT$8,566 total
includes taxes & fees
Sep 7 - Sep 8
NT$11,411
NT$14,813 total
includes taxes & fees
Aug 30 - Aug 31
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
NT$7,829
NT$10,556 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
NT$7,512
NT$10,198 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"
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