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

Search Hotels with Swimming Pool in Islamorada

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Check availability on Islamorada Hotels with Swimming Pool

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Islamorada hotels with a pool

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

1. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,156 reviews)
  • cleanliness
    Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
The price is ₹17,820
₹27,008 total
includes taxes & fees
15 Nov - 16 Nov
Islander Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,495 reviews)
  • cleanliness
    Tropical paradise swim experience awaits with three refreshing pools and poolside service.
The price is ₹21,386
₹31,020 total
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
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, (1,813 reviews)
  • cleanliness
    Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
The price is ₹13,488
₹20,525 total
includes taxes & fees
3 Nov - 4 Nov
Chesapeake Beach Resort
A resort pool with palm trees, beach chairs, and umbrellas.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,327 reviews)
  • cleanliness
    Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
The price is ₹15,039
₹23,881 total
includes taxes & fees
15 Nov - 16 Nov
Amara Cay Resort
A resort with a pool, beach, and ocean view.

5. 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
9.2 out of 10, Wonderful, (303 reviews)
  • cleanliness
    Sparkling pools welcome island adventurers to this oceanfront sanctuary with marina access and private beach lounging areas.
The price is ₹22,752
₹32,553 total
includes taxes & fees
3 Nov - 4 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.

6. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
The price is ₹11,899
₹16,062 total
includes taxes & fees
29 Oct - 30 Oct
La Jolla Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

7. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (303 reviews)
  • cleanliness
    Splash into holiday mode at a Florida Keys gem with 24-hour pool access for endless aquatic adventures.
The price is ₹16,075
₹18,084 total
includes taxes & fees
1 Nov - 2 Nov
Coconut Cove Resort and Marina
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

8. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
The price is ₹14,184
₹19,063 total
includes taxes & fees
29 Oct - 30 Oct
Fisher Inn Resort & Marina
A resort with a pool surrounded by palm trees and a view of the ocean.

9. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Sun-soaked private beach oasis with a sparkling pool for lounging and sipping tropical cocktails.
The price is ₹14,703
₹23,497 total
includes taxes & fees
15 Nov - 16 Nov
La Siesta Resort & Villas
A poolside area with lounge chairs, a barbecue grill, and a view of the ocean.

10. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
The price is ₹18,187
₹25,704 total
includes taxes & fees
4 Nov - 5 Nov
Pines & 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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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, (1813)
The price is ₹13,488
₹20,525 total
includes taxes & fees
3 Nov - 4 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, (1495)
The price is ₹21,386
₹31,020 total
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
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4-star hotels with pools in Islamorada

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1156)
The price is ₹17,820
₹27,008 total
includes taxes & fees
15 Nov - 16 Nov
Islander 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

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

8/10 Good
"We were disappointed in a few things, one being the comfort- the couch in our room was so uncomfortable we couldn’t sit for long at all- it was also dirty with stains- fir the cost if the room, spending some money on a new, comfortable couch with washable cushion covers wouldn’t be too much to ask- plus the resort outdoor furniture was very uncomfortable- the pieces were nice & pretty but could definitely use cushions- we used our bed pillows for our outdoor Adirondack chairs on our balcony. The other disappointment was that there were only 3 kayaks, one was broken and only one of the other two had a back- again, wouldn’t take much to have more available. The staff was wonderful though!!!"
Kelley 4-night trip
Posted 1 hour ago
Fisher Inn Resort & Marina

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.