Find Hotels with an Outdoor Pool in Islamorada, FL

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Top Islamorada Hotels with an Outdoor Pool

The Caribbean Resort
3.5 out of 5
117 Carroll St, Islamorada, FL
4.9/5 Exceptional! (113 reviews)
"Amazing place! Activities pool ocean toys lounging were special! I’ll b back"

Reviewed on Nov 1, 2021

The Caribbean Resort
Casa Morada
3.5 out of 5
136 Madeira Road, Islamorada, FL
The price is $527 per night from Feb 9 to Feb 10
4.8/5 Exceptional! (219 reviews)
"Beautiful location, quiet setting ideal for couples. Good base camp to enjoy attractions and activities in upper and lower keys."

Reviewed on Jan 23, 2022

Casa Morada
Angler's Reef Resort by KeysCaribbean
3.5 out of 5
84977 Overseas Highway, MM 84.9, Islamorada, FL
4.7/5 Exceptional! (12 reviews)
"The pool and the beach are incredible. Great place to stay. Great family vacation spot."

Reviewed on Mar 14, 2021

Angler's Reef Resort by KeysCaribbean
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Islander Resort
3 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is $475 per night from Feb 4 to Feb 5
4.6/5 Exceptional! (1,151 reviews)
"The resort was nice and quiet for the time we stayed there. Clean and comfortable"

Reviewed on Jan 26, 2022

Islander Resort
Islander Bayside Villas and Boatslips
3.5 out of 5
81450 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is $359 per night from Jan 30 to Jan 31
4.5/5 Wonderful! (245 reviews)
"Very well designed and unique. Parking can be challenging, but not troublesome. Nice floor plan. Needs more in the kitchen...utensils, frypans, plates, etc. Easy walking to a couple of good eateries and Bass Pro Shop."

Reviewed on Jan 19, 2022

Islander Bayside Villas and Boatslips
Pines & Palms Resort
3 out of 5
80401 Old Hwy, Islamorada, FL
The price is $319 per night from Feb 3 to Feb 4
4.5/5 Wonderful! (772 reviews)
"Slugs in the bathroom. Other than that, very nice property."

Reviewed on Jan 8, 2022

Pines & Palms Resort
Amara Cay Resort
3.5 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is $306 per night from Feb 28 to Mar 1
4.4/5 Wonderful! (1,058 reviews)
"The staff are excellent- extremely friendly and want to help with everything. Sophie always has a laugh to share."

Reviewed on Jan 25, 2022

Amara Cay Resort
Drop Anchor
3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
The price is $279 per night from Feb 2 to Feb 3
4.4/5 Wonderful! (976 reviews)
"Very nice view of the coast."

Reviewed on Jan 25, 2022

Drop Anchor
Postcard Inn Beach Resort & Marina
3 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is $294 per night from Feb 2 to Feb 3
4.4/5 Excellent! (1,101 reviews)
"This resort is very nice. Management needs to monitor the MUSIC. Outdoor Music should not be turned on before NOON. Most resorts have no music."

Reviewed on Jan 27, 2022

Postcard Inn Beach Resort & Marina
Topsider Resort by Capital Vacations
3.5 out of 5
75500 Overseas Hwy, Islamorada, FL
4.4/5 Excellent! (49 reviews)
"Our stay at Topsider was outstanding. We will definitely visit again."

Reviewed on Jan 23, 2022

Topsider Resort by Capital Vacations
La Jolla Resort
2.5 out of 5
82216 Overseas Highway, Islamorada, FL
The price is $239 per night from Jan 30 to Jan 31
4.4/5 Excellent! (448 reviews)
"Wonderful place to break up a drive down to Key West. Right on the water with a small beach area, kayaks and other amenities. Easy walking distance to a supermarket, several restaurants and two breweries (one is right across the street). Very happy we chose this place for a night."

Reviewed on Jan 26, 2022

La Jolla Resort
Cheeca Lodge & Spa
4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is $219 per night from Jan 30 to Jan 31
4.3/5 Excellent! (991 reviews)
"We were pleasantly surprised with our stay at Cheeca! It was quiet and the staff were very friendly and accommodating. It was set away from the highway enough to give it a "resort feel," and our beachfront room was beautiful!"

Reviewed on Jan 19, 2022

Cheeca Lodge & Spa
Sands of Islamorada
2.5 out of 5
80051 Overseas Highway, Islamorada, FL
The price is $195 per night from Feb 2 to Feb 3
4.3/5 Excellent! (253 reviews)
"Charming little place with wonderful staff. Recently renovated, everything very clean inside and out. Great walk in shower. A real gem. Will definitely stay here again."

Reviewed on Dec 23, 2021

Sands of Islamorada
Pelican Cove Resort & Marina
3 out of 5
84457 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is $280 per night from Feb 27 to Feb 28
4.2/5 Very Good! (981 reviews)
"We liked the amenities of kayaking and biking. We didnt like that there was no housekeeping throughout the stay."

Reviewed on Jan 21, 2022

Pelican Cove Resort & Marina
La Siesta Resort & Marina
3 out of 5
80241 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is $253 per night from Feb 16 to Feb 17
4.1/5 Very Good! (979 reviews)
"The ambiance of this property is really nice and relaxing. Very quaint property with some good options for food and shopping. Unfortunately, the walls/floors are so thin you can hear every conversation. Anyone walking in their room with their shoes on sounded like they were in your room and made ..."

Reviewed on Jan 26, 2022

La Siesta Resort & Marina
Breezy Palms Resort
2.5 out of 5
80015 Overseas Highway, Islamorada, FL
The price is $189 per night from Jan 30 to Jan 31
4/5 Very Good! (47 reviews)
"Excellent!"

Reviewed on Jan 26, 2022

Breezy Palms Resort
Hadley House Islamorada
3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
4/5 Very Good! (580 reviews)
"Great location"

Reviewed on Jan 19, 2022

Hadley House Islamorada
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is $239 per night from Jan 30 to Jan 31
3.7/5 Good! (973 reviews)
"the room was very clean with a nice view. the staff was absolutely great, very caring and accommodating. anna and Sheniqua were freindly, polite and caring. anthony was a good source of information."

Reviewed on Jan 27, 2022

Chesapeake Beach Resort
Fisher Inn Resort & Marina
3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
The price is $254 per night from Feb 1 to Feb 2
3.4/5 (972 reviews)
"We definitely like the scenery out the back door. The staff was super nice. First Place in a long time that knows the definition of "customer service" it was a pleasure to stay there. and We are sending family there to stay as well. only negative was the kayak's was broke (not the places fault) but ..."

Reviewed on Jan 26, 2022

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina
2.5 out of 5
84801 Overseas Highway, Islamorada, FL
The price is $179 per night from Feb 6 to Feb 7
3.4/5 (374 reviews)
"It was a unique hotel with a nice beach. Large area for walking around with a gazebo for sitting."

Reviewed on Jan 19, 2022

Coconut Cove Resort and Marina
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