A beach with white lounge chairs, a covered pavilion, and palm trees.

Islamorada Hotel with Pool

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Check availability on Islamorada Hotel with Pool

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for Islamorada hotels with a pool

A pool area with clear blue water, white lounge chairs, and palm trees.

1. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
The price is HK$5,362
HK$6,606 total
includes taxes & fees
30 Nov - 1 Dec
The Islands of Islamorada
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

2. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,162 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is HK$1,405
HK$2,154 total
includes taxes & fees
15 Nov - 16 Nov
Islander Resort
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

3. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,810 reviews)
"Location is amazing make sure to book a balcony with a view"
United States
Olga Vasiliy
The price is HK$1,184
HK$1,773 total
includes taxes & fees
10 Nov - 11 Nov
Chesapeake Beach Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,511 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is HK$1,421
HK$2,172 total
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.

5. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
The price is HK$873
HK$1,202 total
includes taxes & fees
10 Nov - 11 Nov
La Jolla Resort
An aerial view of a resort with a swimming pool, lounge chairs, and palm trees.

6. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (467 reviews)
"Very helpful staff and great location"
United States
David
The price is HK$1,439
HK$1,708 total
includes taxes & fees
16 Nov - 17 Nov
Casa Morada
A resort with a pool, beach, and ocean view.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (308 reviews)
"Great place to stay!"
United States
Liosbel
The price is HK$1,624
HK$2,401 total
includes taxes & fees
29 Nov - 30 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior

8. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is HK$2,007
HK$2,831 total
includes taxes & fees
9 Nov - 10 Nov
Bayside Villas by Islander Resort
A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

9. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,002 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
The price is HK$1,051
HK$1,439 total
includes taxes & fees
29 Nov - 30 Nov
Hadley Resort and Marina
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

10. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor
9.8 out of 10, Exceptional, (368 reviews)
"We had a great stay. Nice, cosy, and clean. Very quiet, which we loved. Great views from the dock. We will be back!"
Canada
Daniel
The price is HK$1,475
HK$1,880 total
includes taxes & fees
10 Nov - 11 Nov
Kona Kai Resort and Gallery - Adults Only
A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.

11. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (278 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
The price is HK$1,016
HK$1,143 total
includes taxes & fees
18 Nov - 19 Nov
Ragged Edge Resort & Marina
A resort with a pool, palm trees, and beach chairs.

12. Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.6 out of 10, Exceptional, (561 reviews)
"Beautiful place hidden in Tavenier Great staff and the best sunset in the keys"
United States
ED
The price is HK$1,827
HK$2,365 total
includes taxes & fees
10 Nov - 11 Nov
Coconut Palm Inn
A swimming pool with a 5 ft depth marker, surrounded by palm trees and lounge chairs.

13. Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (836 reviews)
"Excellent Stay!"
United States
Annette
The price is HK$1,168
HK$1,491 total
includes taxes & fees
1 Dec - 2 Dec
Atlantic Bay Resort
A resort with a swimming pool, lounge chairs, and palm trees.

14. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,585 reviews)
"We truly enjoyed our stay at Lime Tree Bay. The room was nice and clean and I loved being able to relax in the chairs/hammocks close to the water."
United States
Jessica
The price is HK$971
HK$1,445 total
includes taxes & fees
17 Nov - 18 Nov
Lime Tree Bay Resort
A sunset over a calm body of water with a dock and lounge chairs.

15. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (265 reviews)
"This may be my favorite place I've stayed in the Keys! So quaint and the location and breakfast were amazing. We kayaked to the mangroves, ate at the wonderful restaurant across the street (Ballyhoos), and thoroughly enjoyed the beach area"
United States
Brittany
The price is HK$675
HK$870 total
includes taxes & fees
19 Nov - 20 Nov
Seafarer Key Largo
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.

16. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,206 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
United States
keith
The price is HK$708
HK$796 total
includes taxes & fees
15 Nov - 16 Nov
Rock Reef Resort
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

17. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,002 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
The price is HK$953
HK$1,072 total
includes taxes & fees
29 Nov - 30 Nov
Sunset Cove Beach Resort
A swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

18. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (34 reviews)
"Very friendly staff"
United States
Maria
The price is HK$1,461
HK$1,643 total
includes taxes & fees
16 Nov - 17 Nov
The Ocean View Inn & Pub
A poolside area with lounge chairs, a barbecue grill, and a view of the ocean.

19. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
The price is HK$1,499
HK$2,119 total
includes taxes & fees
15 Nov - 16 Nov
Pines & Palms Resort
A beach with palm trees, a dock, and a boat named "STYX".

20. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,007 reviews)
"Loved the location and the staff were very friendly"
United States
SUSAN
The price is HK$783
HK$881 total
includes taxes & fees
29 Nov - 30 Nov
The Pelican Key Largo Cottages
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.
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Choose what matters most at hotels with a pool in Islamorada

Breakfast included
Hot tub

Hotels with pools and free breakfast in Islamorada

A beach with palm trees and lounge chairs.
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1810)
The price is HK$1,184
HK$1,773 total
includes taxes & fees
10 Nov - 11 Nov
Chesapeake Beach Resort
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Hotels with pools and hot tubs in Islamorada

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1511)
The price is HK$1,421
HK$2,172 total
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
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4-star hotels with pools in Islamorada

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1333)
The price is HK$1,318
HK$2,056 total
includes taxes & fees
15 Nov - 16 Nov
Amara Cay 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.
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Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Perfect halfway stop off for trip to The Keys . Staff exceptionally helpful.. particularly ‘Fran’ I think that was her name on Front Desk. Great pools and loved the bikes ! Rooms were spacious and comfy beds. Recommend Lorelei Restaurant for something to eat off site ..! Great stay, definitely recommend."
Claire 1-night trip
Posted 4 hours ago
Cheeca Lodge & Spa

Frequently asked questions

What's it like visiting Islamorada?
If spending time by the pool is your idea of the perfect getaway, you might want to think about relaxing Islamorada, which offers 125 places to stay with pools. During your visit, you can explore sights such as Bud n' Mary's Dive Center and Robbie's of Islamorada, and then take it easy poolside at one of the accommodation options in Islamorada that guests like for their pools.
What are some accommodation options with pools in Islamorada?
Chesapeake Beach Resort: Features a private beach, 2 outdoor swimming pools and daily. Fisher Inn Resort & Marina: Offers a private beach, a pool and daily. Drop Anchor: Provides free self parking, an outdoor pool and complimentary bicycles. Bayside Villas by Islander Resort: Features 3 restaurants, an outdoor pool and free self parking.
How many pool hotels will I be able to find in Islamorada?
Expedia's 125 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Make a point to visit attractions such as Anne's Beach and MoradaWay Arts & Cultural District. Discover sights such as Bud n' Mary's Dive Center, Robbie's of Islamorada and Fiesta Key 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 the local weather in Islamorada into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.

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