Find Hotels with a Pool in Islamorada, FL
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2 Oct - 4 OctOur 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.
AED 544
AED 818 total
includes taxes & fees
28 Sep - 29 Sep
2. La Jolla Resort
La Jolla ResortMatecumbe
- Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
AED 355
AED 503 total
includes taxes & fees
28 Sep - 29 Sep
3. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
AED 514
AED 847 total
includes taxes & fees
24 Sep - 25 Sep
4. 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.
AED 300
AED 396 total
includes taxes & fees
4 Oct - 5 Oct
5. Pines & Palms Resort
Pines & Palms ResortMatecumbe
- Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
AED 430
AED 686 total
includes taxes & fees
24 Sep - 25 Sep
6. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
AED 522
AED 856 total
includes taxes & fees
28 Sep - 29 Sep
7. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
AED 711
AED 1,048 total
includes taxes & fees
30 Sep - 1 Oct
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.
AED 434
AED 608 total
includes taxes & fees
24 Sep - 25 Sep
View all properties
Hotels with pools and free breakfast in Islamorada
AED 544
AED 818 total
includes taxes & fees
28 Sep - 29 Sep
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
AED 732
AED 1,092 total
includes taxes & fees
29 Sep - 30 Sep
AED 542
AED 610 total
includes taxes & fees
24 Sep - 25 Sep
AED 434
AED 608 total
includes taxes & fees
24 Sep - 25 Sep
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
AED 966
AED 1,289 total
includes taxes & fees
6 Oct - 7 Oct
AED 434
AED 608 total
includes taxes & fees
28 Sep - 29 Sep
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
AED 977
AED 1,301 total
includes taxes & fees
1 Oct - 2 Oct
AED 691
AED 922 total
includes taxes & fees
24 Sep - 25 Sep
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
AED 360
AED 522 total
includes taxes & fees
4 Oct - 5 Oct
AED 333
AED 375 total
includes taxes & fees
24 Sep - 25 Sep
Hotels with pools and hot tubs in Islamorada
AED 542
AED 610 total
includes taxes & fees
24 Sep - 25 Sep
AED 514
AED 847 total
includes taxes & fees
24 Sep - 25 Sep
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
AED 966
AED 1,289 total
includes taxes & fees
6 Oct - 7 Oct
AED 1,488
AED 1,906 total
includes taxes & fees
1 Oct - 2 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
AED 977
AED 1,301 total
includes taxes & fees
1 Oct - 2 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
AED 360
AED 522 total
includes taxes & fees
4 Oct - 5 Oct
AED 458
AED 515 total
includes taxes & fees
24 Sep - 25 Sep
AED 465
AED 627 total
includes taxes & fees
24 Sep - 25 Sep
4-star hotels with pools in Islamorada
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
AED 732
AED 1,092 total
includes taxes & fees
29 Sep - 30 Sep
AED 522
AED 856 total
includes taxes & fees
28 Sep - 29 Sep
AED 711
AED 1,048 total
includes taxes & fees
30 Sep - 1 Oct
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
AED 966
AED 1,289 total
includes taxes & fees
6 Oct - 7 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
AED 977
AED 1,301 total
includes taxes & fees
1 Oct - 2 Oct
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
Fisher Inn Resort & Marina
10/10 Excellent
"This place was the best place to stay I've ever been ever it is wonderful there's nothing not to like about this place the ocean the pool the people the place everybody's so nice and accommodating they will do anything they can to make sure you're happy it's paradise in paradise I would suggest to stay at this place anytime it would be a mistake not to"
Chesapeake Beach Resort
10/10 Excellent
"We had a wonderful stay at this hotel. I stayed with my mom, sister, and niece, and we truly loved the property. The location is great, the hotel is beautiful, and we really enjoyed the amenities and our time together. Overall, it was a very nice experience. The only area I feel could use some improvement is the late checkout process. I requested a late checkout until 2:00 PM because we wanted to enjoy the amenities a little longer before leaving. The property did not appear to be fully booked, so I was hoping there might be some flexibility, but unfortunately my request was not accommodated. By the time I returned to the room, packed everything, and was getting ready to leave, it was close to 1:00 PM. A member of the housekeeping staff knocked on the door and spoke to us in a way that felt rushed and unnecessarily rude, saying, “Don’t you know you were supposed to leave by 11:00 AM?” That interaction made us feel very uncomfortable and was disappointing, especially after such an enjoyable stay. I completely understand that hotels have checkout policies and that late checkout cannot always be guaranteed. However, I believe a little more flexibility when occupancy allows, along with a more courteous approach from housekeeping, would make the guest experience even better. Aside from that situation, we really loved the hotel, the location, and our stay. With a little improvement in communication and hospitality around checkout, it would be an even better experience."
Breezy Palms Resort
10/10 Excellent
"Fantastic place, so clean and the room is beautiful. Gorgeous view!! Love this place!"
Islander Resort
10/10 Excellent
"Loved the property!!! So quiet and relaxing! Great bar, pools, beaches!!!! Would absolutely stay again!"
Amara Cay Resort
8/10 Good
"We had a great stay and overall I would definitely return as it’s a wonderful property. The hotel rooms are spacious and clean. I appreciated the responsiveness of staff and communication via text and ability to make requests via QR code. I would say breakfast was lackluster and the service was extremely slow. Furthermore, I ordered two scrambled eggs and was served powdered eggs which tasted absolutely disgusting. I send that back, and was asked if I would like “hard shell” eggs instead. I thought this was very odd! You wouldn’t expect this at a resort of this level!"
Hadley Resort and Marina
10/10 Excellent
"Si quieres unas vacaciones increíbles , este es el lugar"
Coconut Cove Resort and Marina
10/10 Excellent
"Excellent stay! Love this place and will definitely be back!"
Drop Anchor
10/10 Excellent
"Great resort. Staff were helpful and the location is amazing"