Monroe County

Hotels with Pools in Monroe County

Select your dates to see hotels in Monroe County with a pool for a refreshing break.

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Monroe County Hotels with Swimming Pools

Discover Monroe County hotels with swimming pool for fun and relaxation
Recommended
Lowest price
Closest to downtown
Top reviewed
99+
Hotels in Monroe County
Featured facilities: Exclusive Beach Area, Bar, Spa
Great
106 reviews
9.0/10
1 night
From PLN 685
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99+
Hotels in Monroe County
With a stay at Kingsail Resort, you'll be centrally located in Marathon, within a 10-minute drive of Sombrero Beach and Seven Mile Bridge. This motel is 12.7 mi (20.4 km) from Bahia Honda State Park and 0.7 mi (1.1 km) from Crane Point Museum and Nature Center. Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. Additional amenities at this motel include complimentary wireless internet access, concierge services, and a picnic area. Featured amenities include express check-out, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 44 air-conditioned rooms featuring microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have bathtubs or showers and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.

"Delighted to have stayed 2 nights at the Kingsail Resort. The room was cute and clean with fridge and microwave.   Air conditioning = great!   The pool = great! My daughter and I borrowed 2 kayaks for a one hour ride in the mangroves. It was very pleasant.   We also happily took advantage of the laundry room.   The terrace at the back is well furnished with tables and chairs for reading, having a meal or simply enjoying life. All the furniture is new and comfortable. We observed manatees there during the 2 evenings.   The lady who works at the reception is very nice.   She answered all my questions.   Only one point that could displease, but it was not the case for us: the many “wild” roosters crow before the sun even rises.   We found them rather beautiful with their multi-colored plumage."
Very Good
114 reviews
8.5/10
1 night
From PLN 341
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99+
Hotels in Monroe County
Featured facilities: Exclusive Beach Area, Bar, Spa
Great
111 reviews
9.1/10
1 night
From PLN 683
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99+
Hotels in Monroe County
Featured facilities: Bar, Fitness Room
Very Good
122 reviews
8.7/10
1 night
From PLN 517
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99+
Hotels in Monroe County
Featured facilities: Bar, Fitness Room
Very Good
137 reviews
8.4/10
1 night
From PLN 366
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99+
Hotels in Monroe County
Featured facilities: Bar, Fitness Room
Very Good
116 reviews
8.8/10
1 night
From PLN 443
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65
Hotel near Duval,Key West
Featured facilities: Public Beach, Bar, Massage Room
Amazing
102 reviews
9.6/10
1 night
From PLN 1,114
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99+
Hotels in Monroe County
Featured facilities: Bar, Fitness Room
Very Good
120 reviews
8.9/10
1 night
From PLN 516
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99+
Hotels in Monroe County
Featured facilities: Exclusive Beach Area, Bar
Great
106 reviews
9.2/10
1 night
From PLN 449
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99+
Hotels in Monroe County
Featured facilities: Bar, Fitness Room
Very Good
121 reviews
8.4/10
1 night
From PLN 459
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See All Hotels With Pools in Monroe County

Latest Reviews for Monroe County Hotels

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Find highly-rated hotels with real reviews and ratings to find the perfect stay!

Duval House

9.3/10
Great
Posted on Jul 22, 2025
Guest User
Great place to stay for escape room lovers… Check-in closes at 9pm, and staff clock out. There isn’t a 24hours reception desk, so if you’re driving down be sure to leave plenty of time and get in contact so that you receive your late check-in instructions, unlike us. We arrived at 10pm, to a locked gate, with no idea what the code to get in was, and as we do not have US phones, were unable to call the staff. A guest kindly let us into the resort, and there is a phone on top of a mail box with an out of hours number. After calling, staff were able to talk us through how to get our keys, but the series of steps definitely made it feel like an escape room. Room: Small and compact room. This hotel is laid out like a series of small cabin style huts. To be fair it had all the essentials, and was clean. The sink was in the room separate from the toilet and shower which was a bit strange. All amenities provided. Unfortunately, the AC unit is very loud, but there is also a fan, which is quieter, and tolerable to have on when sleeping. It is hard to sleep with the AC on. Staff were very pleasant and accommodating. Free drinks on check in and check out, no nasty surprises with the resort fee, which is $21.50. Breakfast options were limited, consisting of fruit (melon and pineapple), mini-pastries, granola yoghurt pots and waffles. Instant coffee in flasks. Waffles were made fresh by the staff. Plenty of cats were roaming around the resort. Extras: Only a small car park was available, with about 6 spaces. It costs $30 to park here overnight, but there is street parking available outside for $6/hr between 8am-10pm. You can hire bikes to explore Key West for $15 per day. Location: Very lively location, best location, right in the heart of all the shops, bars and cafes, walking distance to all the attractions.
Price per night fromPLN 387

Paradise Inn - Adult Exclusive

9.0/10
Great
Posted on May 13, 2025
TiChatton
Nice and spacious room included Nespresso pods. Central location, not too far from Duval st. Breakfast included was alright, included hard boiled eggs, cereal, waffle machine, bagels and toast with jam, PB, and cream cheese. Starbucks coffee machine and water machine available throughout the day. Air conditioning fan is a bit loud as the air handler is in the room. No one in the lobby to handle noise complaints at night, especially drunks using the pool after returning from a night out being obnoxious. Charging a resort fee of $34.99, then charging $30 for parking is just an absolute money grab. Should've went with the other options that included the parking, but didn't include breakfast as that breakfast was not worth $34.99...
Price per night fromPLN 414

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

8.9/10
Very Good
Posted on Aug 25, 2025
Guest User
The resort was very beautiful and well maintained. The cottage we stayed in was spacious and we really liked the decor and how soft the beds were. The food was good but a little pricey. We were not impressed with the cabana rental. The cabana was not ready when we arrived. We had to wait for it to be cleaned and set up. The cabana was not labeled and we were confused on which cabana was ours as there were 2 next to each other. We asked when service would start and we were told 10am, then we asked again at 10:45, then went to the front office at 11:30 and when 12pm rolled around with no service we decided to leave and get our money back on the cabana. At that point all we paid for was a chair and towel which did not meet our expectation when spending $250.00 on a cabana for the day. I would recommend several things for the cabana. 1. Number the cabanas so you can clearly see the number. Telling us Cabana 2 does not help when they are beside each other. 2. Stock the min fridge with water. 3. Clearly explain on the cabana rental that food/service will not start until a certain time. We expected to at least get something to drink while in the cabana. 4. Install a call button or app that you can be in contact with someone when you need something. There was a significant delay on getting our refund. And we do appreciate the Manager helping us on Friday get that resolved before we checked out on Saturday morning. All in all, the resort was great. We loved the vibe and updates made to the property. The rooms were comfortable and fresh, and we loved the beds as they were very comfortable, and the sheets were so soft. Everyone was friendly and pleasant. We most enjoyed fish like a local with Patrick. We found that the pool in the middle of the property was less used and felt more quiet and more private therefore we spent our time with a good book. I would give the stay at 4.5 out of 5. Highly recommend trying out Three Waters Resort.
Price per night fromPLN 812

Rock Reef Resort

8.7/10
Very Good
Posted on Aug 21, 2025
Guest User
This was a nice surprise. The location was awesome and accessible to everything that I did over the few days. I was there the hammocks the beach, the pool, the paddle boards, kayaks everything made it well worth staying. The staff were friendly.. parking was abundant. And even though it was on route one, it was set off the road and quiet.
Price per night fromPLN 329

DoubleTree by Hilton Hotel Grand Key - Key West

8.6/10
Very Good
Posted on Nov 14, 2025
Guest User
Very welcoming hotel, complimentary welcome pack with cookie, bottled water, and reusable water bottle upon arrival. Friendly receptionist who speaks French. The pool area and bar/restaurant are very pleasant. Delicious meals and cocktails. Free shuttle to the city center every hour. Highly recommend this hotel 😉
Price per night fromPLN 446

Gilbert's Resort & Marina

8.5/10
Very Good
Posted on May 20, 2026
Guest User
On Balance Gilberts was ok but I would not want to stay more than a couple of days. We where probably not its target customers. The rooms where really nice with a great view but my sister was at the end of the block right by the sewage digester for the resort which made a humming noice which was audible in the room at night, it also smelt really bad in the mornings. Admiralty this could only be smelt outside the room. Suggestion screen the digester and put some filtration for the odour. Plus point they treat the sewage. Thursday night was Ok in the bar although the rock band thought they where playing a stadium, just way too loud, when they stopped and some normality returned the bar shut at 2100, Friday and Saturday, better music but the place was rammed with a lot of kids running around. We would have gone out but the resort is isolated and its almost impossible to get a cab, if you do its very expensive and no guarantee you can get one back. If you have a nominated driver than getting out is an option. Saturday the beach, the bar where just full to bursting, first stop on the Keys out of Miami. A lot of very drunk people having a good time which is fine but if you are not one of them its no fun at all. A visible police presence kept any potential trouble from happening. We where going to go to the pool but there was no room left in the water never mind the side. It is supposed to be for residents and they are supposed to ware a wrist band but that is not enforced, very few in anyone had a wrist band on. In short its not a bad place but don't go if you want a relaxed Keys vibe, stay away from the rooms at the end of the block and only go midweek but only do that if you want to be in bed at 2100. Good points, comfortable rooms, nice views, and very nice staff.
Price per night fromPLN 876

Breezy Palms Resort

8.4/10
Very Good
Posted on Apr 20, 2026
Guest User
We had an amazing relaxing time at Breezy Palms resort!!! We stayed in a 1st floor ocean front apartment that was recently updated, very clean and had a great view of the ocean. Nice to have the full kitchen-used every day. Bathroom was just right and had great shower! Bed was comfortable and great sheets!Screened lanai was perfect. Pool was wonderful, clean and warmer than the ocean! There is nice small beach with sand here. We didn’t get a chance to use the outdoor BBQs, but they looked well maintained, clean, and had everything for grilling. Office staff was friendly and helpful. Fully stocked on site store with bait, snacks, clothing, bottled soft drinks, Blue Bunny ice cream treats, and toiletries. Great maintenance throughout the resort. Although on Route 1, we didn’t hear the highway - lots of roosters and birds chirping. Iguanas were cool to see every day. They have a great dock to fish off of and we did fish for the last 3 days (got a 3 day salt water shore fishing license from nearby bait & tackle store) off the concrete dock and caught a grunt, pinfish, & 28” tarpon - all released. This location was great for seeing all of the keys because it’s a mile marker 80. Walking to nearby restaurants, marina and bridge to see sunset was within 1/4 mile - we could have used the bicycles, but didn’t bring the right footwear for biking. Breezy Palms resort was awesome!! Definitely a place for everyone - couples, families & solo travelers.
Price per night fromPLN 339

Baker's Cay Resort Key Largo, Curio Collection by Hilton

8.4/10
Very Good
Posted on Apr 28, 2019
GBGuest User
We stayed for 2 night which was not enough! The hotel room was spacious, clean and modern with a view over Hammock beach. Delicious buffet breakfast at Calusa... We ate lunch at Dry Rocks... delicious fresh salads, Tacos etc. The staff were very accommodating.. We loved both beaches... coconut beach had lots of sun beds, lots of shade and the sea was lovely and warm. We did paddle board, kayaking and loved it!! Perfect for couples, families etc... Great hotel. Can’t wait to go back.
Price per night fromPLN 981

The Cabana Inn Key West - Adult Exclusive

8.4/10
Very Good
Posted on May 14, 2025
Guest User
Great hotel, very cozy. All entertainment and attractions are nearby, but the hotel itself is not noisy. Good breakfast, happy hour in the evening with wine, cheese and snacks. If there is not enough space for parking near the hotel, then a couple of blocks away you can park for $ 15 per day. Of the nuances - noisy air conditioning in the room and a dirty pool (lots of leaves).
Price per night fromPLN 430

Conch Key Fishing Lodge & Marina

7.7/10
Good
Posted on Dec 22, 2024
Cynthia Ann
I had read the reviews for this hotel on several websites before booking and decided to go with them because they were all good. This was my 60th birthday trip and when we got there this place looked just like their website. Beautiful Old style like you’ll never get to experience ever again. We got a room upgrade to room on the Water. Room #1. There’s nothing fancy about them, but I think that’s what adds to the charm of the hotel but everything in the room is nice, comfortable, clean and works. Patio leads right outside to the water where you can sit on your deck or walk along the pier and look at the boats, we had a boat docked in front of our room. I loved watching the people getting ready to go out. I joked and told them I was happy letting them borrow my boat for the day. We enjoyed our daily Pelican visitors who sat on the post every evening and we enjoyed the Rooster every morning when we sat outside enjoying our ice tea. The pool is very nice, I dipped my foot in and it was a little chilly. The beach area wasn’t much of a beach in my opinion. But it still adds to the charm. Lisa and Tammy were very nice and friendly and we had no problems checking in or any issues whatsoever with our stay. There is a food truck on site we ate at 1st night, because we drove all day and it was real foggy by the time we were going to leave to go eat in Marathon. I had the Crab pizza and Brian had the Ham pizza. $15.00 each and big for one person if your hungry. I didn’t eat all of mine. lol. But very good. The hotel just changed ownership and are doing upgrades and some renovations, so at times while we were there it was a little noisy but nothing we couldn’t deal with. We will definitely stay here again when we go back to the Keys. Because you’re not going to get this Old Style feel staying right on the water for much longer any where else especially for these prices. Pictures our from the deck of our room and one is of our baby sleeping on the comfy bed. Conch Key 🌴.
Price per night fromPLN 293

FAQs

What are some of the best hotels with Swimming Pools in Monroe County?

Whether you are travelling to Monroe County for business or tourism, Fairfield Inn & Suites Marathon Florida Keys (from PLN 516) , La Siesta Resort & Villas (from PLN 540) and Cheeca Lodge & Spa (from PLN 472) are highly recommended among the best hotels.

How much does it cost on average to stay at hotels with Swimming Pools in Monroe County?

For hotels with Swimming Pools in Monroe County, the average price on weekdays is PLN 2,003, and the average price on weekends (Friday - Saturday) is PLN 2,221.

What are the best luxury hotels with Swimming Pools in Monroe County?

If you want to enjoy top services and amenities, there are many luxury hotels with Swimming Pools in Monroe County for you to choose. Cheeca Lodge & Spa (from PLN 472), Isla Bella Beach Resort & Spa - Florida Keys (from PLN 670) and Casa Marina Key West, Curio Collection by Hilton (from PLN 675) are some of the best luxury hotels recommended.

What promotions are available for hotels with Swimming Pools in Monroe County?

Trip.com provides various promotions and discounts for users all year round. You can check the promotions page to see the latest promotions on Trip.com.

Monroe County hotels with Pools information

Total properties557
Number of reviews19,582
Highest pricePLN 6,775
Lowest pricePLN 661
Weekday Avg. PricePLN 2,003
Weekend Avg. PricePLN 2,221