Islamorada Hotel Guide - Hotels with Pool in Islamorada, Florida

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Top Islamorada Hotels with Pool

Amara Cay Resort
Outdoor pool, pool umbrellas, pool loungers

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1198)
"The place was amazing. I enjoyed the time there"
The price is €304
includes taxes & fees
19 Dec - 20 Dec
Amara Cay Resort
Islander Resort
Premium bedding, in-room safe, blackout curtains, free WiFi

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1004)
"It was quiet. Staff were so polite and upbeat. From front desk to towel person to sports sign to bartenders and servers! Disappointed with only one small pool given the cost. Biggest complaint watching a dog poop outside my lanai and a dog peering one foot from my lounge chair. Gross. Dogs were noisier than the people "
The price is €360
includes taxes & fees
13 Jan - 14 Jan 2025
Islander Resort
La Siesta Resort & Villas
Outdoor pool, pool loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1000)
"Great resort!!"
The price is €415
includes taxes & fees
23 Dec - 24 Dec
La Siesta Resort & Villas
Cheeca Lodge & Spa
Property grounds

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1003)
"Excellent vacation resort"
The price is €311
includes taxes & fees
20 Dec - 21 Dec
Cheeca Lodge & Spa
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1000)
"Amazing place! Beautiful area with great amenities. Only thing was really stiff beds. But if you like very firm mattresses…it’s a 5 star. That aside …we will definitely be back!! "
The price is €162
includes taxes & fees
19 Dec - 20 Dec
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Outdoor pool, a heated pool, pool umbrellas, pool loungers

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

3.0 star property
8.0 out of 10, Very good, (1008)
"Excellent and amazing property. I love this resort. Will be back"
The price is €479
includes taxes & fees
19 Dec - 20 Dec
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort
Poolside bar

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (974)
"Place was under heavy construction, when booking stay know one mentioned the whole resort is under reconstruction. Besides the construction the location was beautiful setting "
Pines & Palms Resort
Fisher Inn Resort & Marina
Outdoor pool, a heated pool, open 7:00 AM to 7:00 PM, pool umbrellas

Fisher Inn Resort & Marina

3.5 star property
7.6 out of 10, Good, (1003)
"Great location in the Middle Keys and close to all of the cool hang-outs! Also very clean, has a nice pool and my room had the best balcony view ever!!!"
The price is €176
includes taxes & fees
19 Dec - 20 Dec
Fisher Inn Resort & Marina
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, pool loungers

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (357)
"Wonderful easy to stay resort, just perfect! "
The price is €324
includes taxes & fees
20 Dec - 21 Dec
Islander Bayside Villas and Boatslips
Coconut Cove Resort and Marina
Outdoor pool, pool loungers

Coconut Cove Resort and Marina

2.5 star property
7.4 out of 10, Good, (684)
"I like it"
The price is €170
includes taxes & fees
19 Dec - 20 Dec
Coconut Cove Resort and Marina
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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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 21 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 sunloungers. Drop Anchor: Offers free self parking, an outdoor pool and complimentary bicycles. Fisher Inn Resort & Marina: Provides a private beach, a pool and daily. Sands of Islamorada: Features free self parking, a pool and complimentary wireless Internet access.
How many pool hotels will I be able to find in Islamorada?
Expedia’s 21 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.