Islamorada Hotel Guide - Hotels with Pool in Islamorada, Florida
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28 Aug - 30 AugOur 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.
€194
includes taxes & fees
25 Aug - 26 Aug
2. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
€206
includes taxes & fees
3 Sept - 4 Sept
3. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
€225
includes taxes & fees
23 Aug - 24 Aug
4. La Jolla Resort
La Jolla ResortMatecumbe
- Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
€140
includes taxes & fees
27 Aug - 28 Aug
5. Islander Resort
Islander ResortMatecumbe
- Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
€274
includes taxes & fees
31 Aug - 1 Sept
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.
€113
includes taxes & fees
7 Sept - 8 Sept
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.
€125
includes taxes & fees
20 Sept - 21 Sept
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.
€139
includes taxes & fees
27 Aug - 28 Aug
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Hotels with pools and free breakfast in Islamorada
€194
includes taxes & fees
25 Aug - 26 Aug
€125
includes taxes & fees
20 Sept - 21 Sept
€144
includes taxes & fees
31 Aug - 1 Sept
€134
includes taxes & fees
7 Sept - 8 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
€262
includes taxes & fees
26 Aug - 27 Aug
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
€113
includes taxes & fees
2 Sept - 3 Sept
€140
includes taxes & fees
31 Aug - 1 Sept
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
€278
includes taxes & fees
2 Sept - 3 Sept
€159
includes taxes & fees
2 Sept - 3 Sept
Hotels with pools and hot tubs in Islamorada
€206
includes taxes & fees
3 Sept - 4 Sept
€144
includes taxes & fees
31 Aug - 1 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
€113
includes taxes & fees
2 Sept - 3 Sept
€139
includes taxes & fees
21 Aug - 22 Aug
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
€278
includes taxes & fees
2 Sept - 3 Sept
€164
includes taxes & fees
11 Sept - 12 Sept
€400
includes taxes & fees
21 Aug - 22 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
€299
includes taxes & fees
31 Aug - 1 Sept
€298
includes taxes & fees
21 Aug - 22 Aug
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
€262
includes taxes & fees
26 Aug - 27 Aug
€212
includes taxes & fees
23 Aug - 24 Aug
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
€278
includes taxes & fees
2 Sept - 3 Sept
€400
includes taxes & fees
21 Aug - 22 Aug
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by HiltonKey Largo
€299
includes taxes & fees
31 Aug - 1 Sept
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
Islander Resort
10/10 Excellent
"Gorgeous and relaxing. We had a wonderful time! Staff were super friendly."
Cheeca Lodge & Spa
10/10 Excellent
"The staff were excellent"
Fisher Inn Resort & Marina
10/10 Excellent
"Ok."
Amara Cay Resort
10/10 Excellent
"Great place!"
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
8/10 Good
"Shuttle driver was driving while in personal FaceTime call. Did not move to help with van door which was hard to close. The resort is beautiful and we really enjoyed the amenities."
Breezy Palms Resort
10/10 Excellent
"We were positively surprised when we got to our room to see the wonderful ocean views. The room was quite spacious and appears to have been remodeled quite recently. All was nice and clean and in perfect working order. We will definitely be back."
La Siesta Resort & Villas
8/10 Good
"Great location with many restaurants nearby & close to lots of local attractions. Our room was laid out really well with 2 queen size beds, large closet, & huge TV. Then down a hall into the living room, then to a dining area & kitchen with microwave, small fridge, sink & coffee maker. All in all a well thought out design."
Coconut Cove Resort and Marina
8/10 Good
"Beautiful resort. The pool is gorgeous. Staff went above and beyond to make us comfortable!"
Casa Morada
10/10 Excellent
"It's a beautiful property! A hidden treasure in Islamorada : )"