Hotels with Swimming Pool in Islamorada, Florida

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Top Islamorada Hotels with Swimming Pool

Aerial view
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham

3.0 star property
Key Largo
7.6 out of 10, Good, (1003)
"clean room nice balcony view nice staff nice breakfast"
United States
Manuel
The price is P5,973
P8,593 total
includes taxes & fees
Nov 23 - Nov 24
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 star property
Long Key
9.2 out of 10, Wonderful, (1091)
"Excellent stay! "
United States
Joshua
Lime Tree Bay Resort
Outdoor spa tub
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1575)
"Great breakfast very well kept grounds"
United States
James
The price is P8,359
P12,726 total
includes taxes & fees
Nov 18 - Nov 19
Chesapeake Beach Resort
Exterior detail
Rock Reef Resort

Rock Reef Resort

2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1060)
"Everything clean, friendly staff"
United States
Arlene
Rock Reef Resort
View from room
La Jolla Resort

La Jolla Resort

2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (1003)
"Great place to stay lovely staff Easy to find "
United Kingdom
diane
La Jolla Resort
Terrace/patio
Bayside Inn Key Largo

Bayside Inn Key Largo

3.0 star property
Key Largo
8.6 out of 10, Excellent, (1606)
"Great location and helpful staff !"
United States
Nikki
The price is P7,618
P10,047 total
includes taxes & fees
Nov 20 - Nov 21
Bayside Inn Key Largo
3 bars/lounges, poolside bar
Amara Cay Resort

Amara Cay Resort

4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1255)
"The rooms were clean, staff was friendly and helpful, food was delicious, the property was beautiful and loved how there was connections to the other resorts through van transportation or the Rum runner boat! Would definitely stay again! "
United States
Lucia
The price is P9,128
P14,190 total
includes taxes & fees
Nov 30 - Dec 1
Amara Cay Resort
Outdoor pool
Treasure Harbor

Treasure Harbor

3.0 star property
Islamorada
9.0 out of 10, Wonderful, (111)
"The houseboat was so cute! The staff was very friendly and helpful. We really enjoyed out stay. The pool was new and clean. We would definitely come back."
United States
Tracie
Treasure Harbor
Exterior
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 star property
Islamorada
8.2 out of 10, Very Good, (1004)
"Great experience, highly recommend staying at the Fisher Inn."
United States
Eduardo
The price is P6,059
P8,743 total
includes taxes & fees
Dec 18 - Dec 19
Fisher Inn Resort & Marina
Exterior
Breezy Palms Resort

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (567)
"Best hotel for the price"
United States
luzdari
The price is P3,894
P7,442 total
includes taxes & fees
Nov 18 - Nov 19
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.
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Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"We loved this resort! It was relaxing, but also has tons of activities to keep everyone entertained. Three pools, two hot tubs, tennis, pickle, golf, beach, paddle boards, kids activities. Staff was gracious and helpful. We loved being able to have lunch and drinks served at the pools. And, if you are a swimmer, they have an adult only lap pool. Jessica, the concierge, was especially helpful to us after we made a reservation the night before, as we had to quickly move out of our terrible VRBO in Marathon. She explained our room choices and even enabled an early check in. Thanks Jessica! We will be back!"
Jennifer 3-night trip
Posted 2 days ago
Cheeca Lodge & Spa

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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 136 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 136 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 Founders Park. Discover sights such as Bud n' Mary's Dive Center, Anne's Beach, 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 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.