Monroe County Hotels with Pools
If you want a relaxing stay, pick a hotel in Monroe County that has a pool. You can swim or rest by the water anytime you like. Look for places with well-kept pools to improve your experience.
Trip.com Featured hotels with Swimming Pools in Monroe County
1. Havana Cabana at Key West
• Rated 8.7/10 from 112 reviews.
• Only Key West Tropical Forest & Botanical Garden to 1.36 km.
2. Fairfield Inn & Suites Marathon Florida Keys
• Offers Carbon monoxide alarm, Bar, and Conference room.
• Rated 8.5/10 based on 119 reviews.
• Convenient to Sombrero Reef, only 0.17 km.
3. Cheeca Lodge & Spa
• Rated 8.9/10 based on 108 reviews.
• Convenient to Clearly Unique Charters, only 0.15 km.
The above hotel prices are based on Trip.com for June 12-June 18.
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Highest Rated
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 Crane Point Museum and Nature Center. This motel is 1.4 mi (2.2 km) from Boot Key Harbor and 1.4 mi (2.3 km) from Marathon Air Museum.
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.
"This establishment is not a resort
But it's a basic motel that doesn't deserve this price per night.
Small room, very ordinary bathroom.
No breakfast, and the welcome was not very warm."
Very Good
114 reviews
8.4/10
99+
Great
106 reviews
9.0/10
99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar, Massage room, Gym
Great
100 reviews
9.2/10
99+
Hotels in Monroe County
Featured facilities: Bar, Spa, Gym
Very Good
133 reviews
8.5/10
31
Hotels in Monroe County
With a stay at Sugar Loaf Lodge in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Sound. This hotel is 0.6 mi (1 km) from Lower Sugarloaf Sound and 2.5 mi (4 km) from Upper Sugarloaf Key.
Take advantage of recreation opportunities including outdoor tennis courts and an outdoor pool. This hotel also features complimentary wireless internet access, tour/ticket assistance, and a vending machine.
At Sugar Loaf Lodge, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge.
The front desk is staffed during limited hours. Free self parking is available onsite.
Make yourself at home in one of the 31 air-conditioned rooms featuring flat-screen televisions. Rooms have private balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with shower/tub combinations are provided.
Very Good
100 reviews
8.2/10
1 night
From DKK 1,062
99+
Hotels in Monroe County
With a stay at Old Wooden Bridge Resort and Marina in Big Pine Key (Punta Brisa), you'll be within a 15-minute drive of Florida Keys Beaches and Blue Hole. This cottage is 2.7 mi (4.4 km) from National Key Deer Refuge Visitor Center and 2.9 mi (4.7 km) from Big Pine Key Flea Market.
Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional features at this cottage include complimentary wireless internet access, shopping on site, and a picnic area.
The front desk is staffed during limited hours. Free self parking is available onsite.
Make yourself at home in one of the 12 individually decorated guestrooms, featuring microwaves and flat-screen televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms have bathtubs or showers and complimentary toiletries. Conveniences include coffee/tea makers, and housekeeping is provided on request.
Very Good
100 reviews
8.6/10
99+
Very Good
103 reviews
8.7/10
99+
Very Good
119 reviews
8.7/10
99+
Very Good
105 reviews
8.8/10
77
Very Good
102 reviews
8.3/10
Latest Reviews for Monroe County Hotels
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Read genuine traveler ratings & reviews to find your perfect stay.
9.1/10
Great
GGuest UserGreat 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.
8.9/10
Very Good
GGuest UserThe 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.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Hotel near Islamorada
Price per night from:0
8.7/10
Very Good
GGuest UserI chose the hotel instead of one in Key West because it offers a shuttle service to the center and has a larger pool. However, it was fully booked on our evening. We had to wait 2 hours and let 3 buses go. The shuttle back was just as full. We walked the long way back to the meeting point and then it left right in front of us without us. So if you're only staying 1-2 days, you're out of luck. The room was ultra dark but large. You can hear the planes very clearly during the day, and directly. They're big planes and they fly every 20 minutes.
Otherwise, it's OK. Don't expect much from the breakfast, coffee is available all day in the lobby
8.7/10
Very Good
GGuest UserThis 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.
8.3/10
Very Good
GGuest UserOn 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.
8.3/10
Very Good
GGuest UserWe 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.
8.2/10
Very Good
GGuest UserGreat 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).
8.2/10
Very Good
GGuest UserNice place. Great location. Friendly staff. Comfortable room. Parking is NOT included. I'm a bit annoyed about that because I didn't find anything about that when reserving the room. I even called and left a message on the concierge line asking about parking but never got a callback.
7.7/10
Good
CCynthia AnnI 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 🌴.
FAQs
Where is the best place for a stay with Swimming Pools in Monroe County?
Whether you are traveling to Monroe County for business or fun, Havana Cabana at Key West (from DKK 940) , Fairfield Inn & Suites Marathon Florida Keys (from DKK 1,147) and Hampton Inn Key Largo (from DKK 781) are all preferred hotels.
What’s the typical price for hotels with Swimming Pools in Monroe County?
For hotels with Swimming Pools in Monroe County, the average price on weekdays is DKK 3,788, and the average price on weekends (Friday–Saturday) is DKK 5,108.
What’s the best romantic hotels in Monroe County with Swimming Pools?
Many hotels with Swimming Pools in Monroe County have good vibes, suitable for couples in need of a romantic escape. If you are planning to celebrate an anniversary, The Laureate Key West (from DKK 1,098) is a preferred hotel.
What's the best high-end place with Swimming Pools to stay in Monroe County?
There are many luxury hotels with Swimming Pools in Monroe County. Cheeca Lodge & Spa (from DKK 1,073), Isla Bella Beach Resort & Spa - Florida Keys (from DKK 1,382) and Playa Largo Resort & Spa, Autograph Collection (from DKK 1,845) are very popular.
What are some great hotel promotions for property 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 what promotions are available on Trip.com.
Monroe County Hotels with Pools Information
| Total properties | 454 |
|---|---|
| Number of reviews | 17,086 |
| Highest price | DKK 11,208 |
| Lowest price | DKK 1,124 |
| Weekday Avg. Price | DKK 3,788 |
| Weekend Avg. Price | DKK 5,108 |