Hotels with Swimming Pool in Islamorada, Florida

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Check availability on Islamorada Hotels with Swimming Pool

Tonight
Oct 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Top Islamorada Hotels with Swimming Pool

Cheeca Lodge & Spa
Property grounds

Cheeca Lodge & Spa

5.0 star property
9.2 out of 10, Wonderful, (1208)
"Beautiful and relaxing hotel!!"
The price is P6,920
P11,710 total
includes taxes & fees
Oct 5 - Oct 6
Cheeca Lodge & Spa
Rock Reef Resort
Exterior detail

Rock Reef Resort

2.5 star property
9.2 out of 10, Wonderful, (1025)
"Old place but amazing views, clean rooms, nice staff "
Rock Reef Resort
Chesapeake Beach Resort
Outdoor spa tub

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1529)
"Wonderful property, breakfast was awesome "
The price is P7,679
P11,909 total
includes taxes & fees
Oct 5 - Oct 6
Chesapeake Beach Resort
Ragged Edge Resort & Marina
Exterior

Ragged Edge Resort & Marina

2.5 star property
9.4 out of 10, Exceptional, (193)
"We enjoyed our stay very much and have already recommended this hotel to friends. Thanks for accommodating our check in and check out. "
Ragged Edge Resort & Marina
Creekside Inn
Fishing

Creekside Inn

2.5 star property
8.0 out of 10, Very Good, (1000)
"We will definitely stay here again"
The price is P6,623
P7,451 total
includes taxes & fees
Oct 5 - Oct 6
Creekside Inn
La Jolla Resort
View from room

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1000)
"The location is great..nice beach and dock area..room was very nice.. will definitely plan to return for a longer stay"
La Jolla Resort
Lime Tree Bay Resort
Exterior

Lime Tree Bay Resort

3.5 star property
9.2 out of 10, Wonderful, (1094)
"So close to the ocean was amazing. "
Lime Tree Bay Resort
Kona Kai Resort and Gallery - Adults Only
Exterior

Kona Kai Resort and Gallery - Adults Only

2.5 star property
9.8 out of 10, Exceptional, (260)
"Property was very clean including beach, pool, and grounds."
Kona Kai Resort and Gallery - Adults Only
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Aerial view

Dove Creek Resort & Marina, Trademark Collection by Wyndham

3.0 star property
7.6 out of 10, Good, (1001)
"Great place to stay!"
The price is P4,893
P7,349 total
includes taxes & fees
Oct 9 - Oct 10
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (541)
"Spacious rooms and location was great for what we needed. "
The price is P4,472
P8,045 total
includes taxes & fees
Oct 5 - Oct 6
Breezy Palms Resort
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 properties

Top Islamorada Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"Truly enjoyed our visit to this property. Lots to do and great dining options! We will be back."
Kimberlie Kaye 4-night trip
Posted 3 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Islamorada?
If taking it easy by the pool is your idea of the perfect getaway, you might want to think about relaxing Islamorada, which offers 107 places to stay with pools. During your trip, you can explore sights such as Bud n' Mary's Dive Center and Islamorada County Park, and then relax and unwind poolside at one of the accommodations in Islamorada that guests like for their pools.
What are some accommodations with pools in Islamorada?
Chesapeake Beach Resort: Features a private beach, 2 outdoor pools, and daily. Fisher Inn Resort & Marina: Offers a private beach, a pool, and daily. Bayside Villas by Islander Resort: Provides 3 restaurants, an outdoor pool, and free self parking. Drop Anchor: Features free self parking, an outdoor pool, and complimentary bicycles. Sands of Islamorada: Offers free self parking, a pool, and complimentary wireless internet access.
How many pool hotels should I expect to find in Islamorada?
Expedia's 107 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Spend some time experiencing the great outdoors at Islamorada County Park and Anne's Beach. Discover sights such as Bud n' Mary's Dive Center, Fiesta Key, and Everglades National Park during your stay. Islamorada appeals to visitors with its beautiful ocean views and top seafood restaurants.
When is the best time to book a hotel with a pool in Islamorada?
Taking into account the local weather in Islamorada is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.