Monroe County Hotels with Pools
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Amazing 9+Great 8+Good 7+Pleasant 6+Best Monroe County Hotels with Swimming Pools
Check out our selection of Monroe County hotels with Pools
Most Booked
Lowest price
Closest to downtown
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.
"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
113 reviews
8.4/10
1 night
From US$98
99+
Great
106 reviews
9.0/10
1 night
From US$129
99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar, Massage Room, Fitness Room
Great
100 reviews
9.0/10
1 night
From US$259
99+
Hotels in Monroe County
Featured facilities: Bar, Spa, Fitness Room
Very Good
133 reviews
8.4/10
1 night
From US$189
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
8.0/10
1 night
From US$164
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
8.4/10
1 night
From US$116
99+
Very Good
103 reviews
8.7/10
1 night
From US$275
99+
Hotels in Monroe County
Featured facilities: Bar, Fitness Room
Very Good
119 reviews
8.5/10
1 night
From US$180
99+
Hotels in Monroe County
Featured facilities: Bar, Spa, Fitness Room
Very Good
105 reviews
8.7/10
1 night
From US$179
77
Very Good
102 reviews
8.1/10
1 night
From US$123
Top rated hotels in Monroe County
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Explore genuine reviews and ratings from real travellers to find the perfect accommodation for your needs.
9.0/10
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.
8.8/10
Very Good
TTiChattonNice 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...
8.7/10
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:US$305
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
8.6/10
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.
8.6/10
Very Good
GGuest UserHotel had a great vibe, filled with plants and was very colorful in the lobby, a true feeling to the name, Havana cabana. The pool was the best part, so clean and had inner tubes to float around and relax. Two complimentary drink passes during check in was a plus. Food was excellent for lunch and breakfast. We went as a family trip so the only downside was there weren't a lot of kids. At one point we thought it was ”adult only” but then towards the later afternoon we started to see more kids. Rooms were clean and service was good. Definitely will stay again.
8.5/10
Very Good
GGuest UserVery 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 😉
8.4/10
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.
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Hotel near Key Largo
Price per night from:US$362
8.1/10
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).
7.6/10
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 🌴.
Frequently Asked Questions
What's the best hotel with Swimming Pools in Monroe County?
Whether your trip to Monroe County is for business or leisure, Cheeca Lodge & Spa (from US$166) , Fairfield Inn & Suites Marathon Florida Keys (from US$177) and Havana Cabana at Key West (from US$148) are popular choices.
What's the best romantic hotel with Swimming Pools in Monroe County?
Monroe County has many options for couples to choose a stay with Swimming Pools. If you plan to celebrate an anniversary, The Laureate Key West (from US$170) can be a good choice.
What's the average price for hotels with Swimming Pools in Monroe County?
For hotels with Swimming Pools in Monroe County, the average price is US$595 on weekdays and US$815 on weekends (Friday–Saturday).
Which hotels with Swimming Pools in Monroe County have deals?
There are many deals available on Trip.com for both new and loyal users. Please check the promotions page to save your upcoming stays.
What's the best luxury hotel with Swimming Pools in Monroe County?
Monroe County has many luxury hotels with Swimming Pools. Cheeca Lodge & Spa (from US$166), Playa Largo Resort & Spa, Autograph Collection (from US$404) and Casa Marina Key West, Curio Collection by Hilton (from US$244) are popular choices.
Monroe County Hotels with Pools Information
| Total properties | 467 |
|---|---|
| Number of reviews | 16,761 |
| Highest price | US$2,192 |
| Lowest price | US$192 |
| Weekday Avg. Price | US$595 |
| Weekend Avg. Price | US$815 |
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