Find Hotels with a Pool in Islamorada, FL

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Check availability on Islamorada Hotels with a Pool

Tonight
25 Jan - 26 Jan
Tomorrow
26 Jan - 27 Jan
Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb

Our top choices for Islamorada hotels with a pool

Outdoor pool

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (126 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor
Exterior detail

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,080 reviews)
"Nice place to spend some time in the Keys conveniently located,clean rooms and helpful staff with excellent views of Bay."
United States
Harry
Rock Reef Resort
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, (1,005 reviews)
"Staff was courteous, room was clean & ready when we arrived. "
United States
Kathy
The price is AED 590
AED 780 total
includes taxes & fees
1 Feb - 2 Feb
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Beach/ocean view

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,655 reviews)
"Wonderful breakfast with omelettes cooked to order, great pancakes, fresh fruit, etc. very pleasant staff and beautiful beach area."
United States
Kurt
The price is AED 694
AED 988 total
includes taxes & fees
27 Jan - 28 Jan
Chesapeake Beach Resort
Terrace/patio

Bahia Bay Resort

Bahia Bay Resort
2.5 star property
Rock Harbor
8.8 out of 10, Excellent, (136 reviews)
"Very clean and roomy rooms. The pool is warmest pool in Florida. Will be back every year. Thank You Mike!"
United States
Mark
Bahia Bay Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,007 reviews)
"Great"
United States
Kelly
The price is AED 577
AED 778 total
includes taxes & fees
29 Jan - 30 Jan
Drop Anchor
Outdoor pool, sun loungers

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"This place is amazing "
United States
cindy
La Jolla Resort
Exterior

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,664 reviews)
"Spotless rooms, staff is so friendly and helpful! Amazing place to stay."
Canada
Jeannie
The price is AED 698
AED 877 total
includes taxes & fees
4 Feb - 5 Feb
Bayside Inn Key Largo
Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,140 reviews)
"Beautiful resort on the beach and everything was perfect ."
United States
Vinatha
Lime Tree Bay Resort
Private beach, white sand, sun loungers, beach towels

Bay Harbor Lodge

Bay Harbor Lodge
3.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (664 reviews)
"Staff and Cleanliness - outstanding!"
United States
Jon
The price is AED 716
AED 806 total
includes taxes & fees
26 Jan - 27 Jan
Bay Harbor Lodge
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
Ocean view

Hotels with pools and free breakfast in Islamorada

Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1655)
The price is AED 694
AED 988 total
includes taxes & fees
27 Jan - 28 Jan
Chesapeake Beach Resort
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Hotels with pools and ocean views in Islamorada

Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1655)
The price is AED 694
AED 988 total
includes taxes & fees
27 Jan - 28 Jan
Chesapeake Beach Resort
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Hotels with pools and hot tubs in Islamorada

Exterior
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1000)
The price is AED 1,848
AED 2,281 total
includes taxes & fees
8 Feb - 9 Feb
Playa Largo Resort & Spa, Autograph Collection
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The workers were excellent. The breakfast staff were wonderful. Chris, Didi,Emily. The were so helpful. You have a great bunch of workers. I can't say enough about the staff. "
Donna 7-night trip
Posted 1 day ago
Chesapeake Beach Resort

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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 Everglades National Park and Florida Keys Brewing Co., 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. 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. 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?
Explore places like Everglades National Park while you're in Islamorada. Enjoy a stroll along the shore at Anne's Beach and Sunset Drive Beach. 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.