Find Hotels with a Pool in Florida Keys

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Check availability on Florida Keys Hotels with a Pool

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Top Florida Keys Hotels with a Pool

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1482)
"We absolutely loved our stay here! Great pools and beach access, delicious breakfast every morning (made to order omelets!), very quiet and super short drive to anywhere we wanted to go on the island. Staff was always so helpful and checked in on us via text throughout our stay. Would absolutely recommend to others and stay again ourselves. "
Stacy
$183 nightly
The price is $206
Aug 3 - Aug 4
Total includes taxes and fees
Chesapeake Beach Resort

Southwinds Motel

2.0 star property
8.8 out of 10, Excellent, (1113)
"My room was very clean and the bed was extremely comfortable. The bathroom was a little small for me but im a 6'4" big guy. Great bar right on the property. Close proximity to just about anywhere a tourist would want to go. Very nice
pool
. Every guest was very friendly. Staff is extremely helpful and friendly. I loved my stay. I recommend to anyone who wants to visit key west. "
Steven
$162 nightly
The price is $183
Jul 15 - Jul 16
Total includes taxes and fees
Southwinds Motel

Ibis Bay Beach Resort

2.5 star property
8.2 out of 10, Very Good, (1996)
"It was a good place. Excellent staff. The best part was the
pool
and the
pool
’s bar. Good food and drinks. "
Adrian
$150 nightly
The price is $169
Jul 10 - Jul 11
Total includes taxes and fees
Ibis Bay Beach Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1121)
"We had a great time here. Great for the kids to swim, run around and also be beach side and play in a sand box. Live music in the evenings was a big hit and the food was excellent on site at every restaurant. Downsides- I thought the
pool
area could use an upgrade (lounge chairs and things are old and could be so much more beautiful) and when trying to coordinate kids activities and sitters, they were not helpful at all and the people at the kid area were young and not very good at customer...
Ryan
$239 nightly
The price is $269
Aug 6 - Aug 7
Total includes taxes and fees
Cheeca Lodge & Spa

Lime Tree Bay Resort

3.5 star property
9.2 out of 10, Wonderful, (1090)
"Adorable resort for a very reasonable price. Location is terrific, half way through the keys outside of Islamorada and just a little over an hour from Key West. Very attentive staff, fantastic place to watch sunset. Large outdoor area with
pool
and plenty of seating all around the property. Will definitely stay there again."
Carol
$164 nightly
The price is $185
Jul 27 - Jul 28
Total includes taxes and fees
Lime Tree Bay Resort

Rainbow Bend Resort

2.5 star property
8.2 out of 10, Very Good, (681)
"We stayed here after spending 4 nights in Key Largo. The property is an older vacation resort in a great location. We enjoyed hanging outside with a fantastic water view better when the tide is up. The smell of the seagrass at times was a bit harsh, but when you have breezes it's not as bad. The
pool
is nice and a great place to cool off. We very much enjoyed our 5 night stay here before heading to Key West."
Eileen
$133 nightly
The price is $150
Jul 10 - Jul 11
Total includes taxes and fees
Rainbow Bend Resort

Simonton Court Historic Inn & Cottages

2.5 star property
9.8 out of 10, Exceptional, (771)
"The room was beautiful and updated. The pools were clean and very convenient to the rooms. The beautiful garden walkway was amazing! The best part of our stay was the staff! Everyone was so friendly and went out of their way way to ensure we were comfortable and had everything we could possibly need. One in particular took the time to educate us on the gorgeous orchids on the property and because of Norman’s knowledge I plan on coming back again in April to see the beautiful orchids bloom. It by...
Jenny
$166 nightly
The price is $187
Jul 13 - Jul 14
Total includes taxes and fees
Simonton Court Historic Inn & Cottages

Southernmost Beach Resort and Guesthouses

4.0 star property
8.6 out of 10, Excellent, (2609)
"The staff was wonderful helped with anything we asked! So many fun games at the pools! Close to so many things! Really had a great time!"
susan
$259 nightly
The price is $291
Aug 4 - Aug 5
Total includes taxes and fees
Southernmost Beach Resort and Guesthouses

Waterside Suites & Marina

3.5 star property
8.8 out of 10, Excellent, (1012)
"The king bed upstairs was very comfortable. Location was perfect. We close to all the dive charters and walkable to skippers dock side for drinks. Having a balcony overlooking the canal was nice. The ac was a bit loud when it kicked on but kept the unit nice and cool. The
pool
is simple but well maintained. "
Shannon
$118 nightly
The price is $133
Aug 3 - Aug 4
Total includes taxes and fees
Waterside Suites & Marina

The Southernmost Inn - Adults Only

3.0 star property
8.2 out of 10, Very Good, (1116)
"I had An amazing time at this property and it offers a great breakfast, all day two pools, and a hot tub that is open all night and day."
Thomas
$150 nightly
The price is $169
Jul 13 - Jul 14
Total includes taxes and fees
The Southernmost Inn - Adults Only
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.