Search Hotels with Pool in Islamorada

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Check availability on Islamorada Hotels with Pool

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Islamorada hotels with a pool

Exterior detail
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1072)
"Great room, friendly staff "
United States
Chengdao
Rock Reef Resort
Aerial view
Dove Creek Resort & Marina, Trademark Collection by Wyndham

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, (1005)
"Great room with beautiful sunrise over the ocean! "
Canada
Heather
The price is Rp2.262.546
Rp3.076.221 total
includes taxes & fees
8 Jan - 9 Jan 2026
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior
Lime Tree Bay Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1108)
"This place is the best kept secret "
United States
Kathleen
Lime Tree Bay Resort
Outdoor pool
Treasure Harbor

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (118)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
Treasure Harbor
Outdoor spa tub
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1601)
"The entire resort was wonderful."
Canada
Mat
The price is Rp3.164.886
Rp4.502.178 total
includes taxes & fees
6 Jan - 7 Jan 2026
Chesapeake Beach Resort
Superior Bungalow, Multiple Beds, Beachfront (Ground Level Sleeps 6) | View from room
La Jolla Resort

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (1002)
"Great stay. Friendly staff, great accommodations, very nice complex. "
United States
Shela
La Jolla Resort
Fishing
Creekside Inn

Creekside Inn

Creekside Inn
2.5 star property
Tavernier
8.0 out of 10, Very good, (1004)
"The room was nice, but walking out to the pier from door was excellent "
United States
Anthony
The price is Rp2.546.292
Rp2.864.578 total
includes taxes & fees
5 Jan - 6 Jan 2026
Creekside Inn
Outdoor pool, open 8:00 AM to 11:00 PM, pool loungers
Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1008)
"Clean rooms, nice views"
United States
Roger
The price is Rp3.035.980
Rp3.716.815 total
includes taxes & fees
6 Jan - 7 Jan 2026
Ocean Pointe Suites at Key Largo
Oceanfront King Suite w/ Kitchen & Private Balcony | Water view
Drop Anchor

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1003)
"Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! "
United States
Laura
The price is Rp2.352.060
Rp3.232.001 total
includes taxes & fees
11 Jan - 12 Jan 2026
Drop Anchor
Terrace/patio
Bayside Inn Key Largo

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1625)
"Great location, Relaxing friendly atmosphere. Very basic room amenities but beautiful beach, pool, experience "
United States
Rebecca
The price is Rp2.712.042
Rp3.469.573 total
includes taxes & fees
4 Jan - 5 Jan 2026
Bayside Inn Key Largo
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

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

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

10/10 Excellent
"Beautiful chilled out hotel"
Jacqueline 2-night trip
Posted 4 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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 135 places to stay with pools. During your visit, you can explore sights such as Everglades National Park and Florida Keys Brewing Co., 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. 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 will I be able to find in Islamorada?
Expedia's 135 hotels in Islamorada give you a great choice for your poolside getaway.
What is there to see and do in Islamorada?
Explore places such as 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 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.