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Featured Islamorada Hotels with an Outdoor Pool

See all 358 Properties in Islamorada

Estimated price for 1 night/2 adults

Amara Cay Resort
Amara Cay Resort
3.5 out of 5.0 80001 Overseas Hwy, Islamorada, FL
4.3/5 (1695 reviews)
$204/ night for 2 guests

I didn’t know what to expect but found the property to be very comfortable and open. The only complaint I can make is the music playing in the bar area was really boring.

Reviewed on Jun 20, 2019
Islander Resort
Islander Resort
3.0 out of 5.0 82100 Overseas Highway, Islamorada, FL
Free Cancellation
4.2/5 (1747 reviews)
$249/ night for 2 guests

The Islander Resort is top notch. Friendly staff, clean facility, great location and good food and drinks at reasonable rates. I can’t imagine staying anywhere else whenever we go back to The Keys. They’ve set a bar that’s going to be hard to beat.

Reviewed on Jun 22, 2019
La Siesta Resort & Marina
La Siesta Resort & Marina
3.0 out of 5.0 80241 Overseas Highway, Islamorada, FL
3.9/5 (809 reviews)
$184/ night for 2 guests

Property is in a nice location in Islamorada. Pool was nice and gave good views of the ocean. Plenty of seating options. We were told they were sold out yet we were upgraded to an ocean room. Not exactly sure how that works but it was nice of them to do that. Couple of small gripes. WIFI was nonexistent. ...

Reviewed on Jun 20, 2019
Drop Anchor
Drop Anchor
3.0 out of 5.0 84959 Overseas Highway, 222, Islamorada, FL
4.3/5 (1172 reviews)
$143/ night for 2 guests

A little bit of paradise, the staff were lovely and very helpful, pool area clean and tidy wonderful sandy area with seating and hammocks (I did manage to get in and out without falling on my face) accommodation has full kitchen also BBQ's on site for customer use.

Reviewed on Jun 23, 2019
Pines & Palms Resort
Pines & Palms Resort
3.0 out of 5.0 80401 Old Hwy, Islamorada, FL
4.4/5 (515 reviews)
$129/ night for 2 guests

Nice and quiet, great pool. Went fishing with Captain Chris and he was determined to find the fish we wanted to fish for, and he did!

Reviewed on Jun 10, 2019
Pelican Cove Resort & Marina
Pelican Cove Resort & Marina
3.0 out of 5.0 84457 Overseas Highway, Islamorada, FL
4.0/5 (1241 reviews)
$194/ night for 2 guests

Property was amazing! Very clean and friendly staff. The on site restaurants and bars where amazing and did not disappoint. The rooms are spacious and the beds are comfortable. We will defiantly go back.

Reviewed on Jun 24, 2019
Cheeca Lodge & Spa
Cheeca Lodge & Spa
4.0 out of 5.0 81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
4.4/5 (1689 reviews)
$215/ night for 2 guests

Beautiful grounds, clean and upgraded rooms, friendly staff.

Reviewed on Jun 21, 2019
Postcard Inn Beach Resort & Marina
Postcard Inn Beach Resort & Marina
3.0 out of 5.0 84001 Overseas Hwy, Islamorada, FL
3.8/5 (1363 reviews)
$189/ night for 2 guests

We liked the beach and swim up bar. We did not like the l

Reviewed on Jun 24, 2019
Fisher Inn Resort & Marina
Fisher Inn Resort & Marina
2.5 out of 5.0 84951 Overseas Hwy, Islamorada, FL
3.0/5 (922 reviews)
$127/ night for 2 guests

Very clean and looks exactly like the pictures. Plenty of things to do on property. Relaxing atmosphere. Most rooms are on the second floor without an elevator so people with needs should request a cottage.

Reviewed on Jun 20, 2019
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Hotels with an Outdoor Pool: Our travelers loved these

Estimated price for 1 night/2 adults

Recently booked Hotels with an Outdoor Pool in Islamorada

La Siesta Resort & Marina
3.0 out of 5.0
Last booking: 1 hour ago
Pines & Palms Resort
3.0 out of 5.0
Last booking: 1 hour ago
Cheeca Lodge & Spa
4.0 out of 5.0
Last booking: 2 hours ago
Drop Anchor
3.0 out of 5.0
Last booking: 3 hours ago
Creekside Inn Islamorada
2.5 out of 5.0
Last booking: 4 hours ago
Amara Cay Resort
3.5 out of 5.0
Last booking: 4 hours ago
Hadley House Islamorada
3.0 out of 5.0
Last booking: 5 hours ago
Islander Resort
3.0 out of 5.0
Last booking: 11 hours ago
La Jolla Resort
2.5 out of 5.0
Last booking: 20 hours ago

Pocket Guide: Hotels with an Outdoor Pool in Islamorada

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