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+
Very Good
107 reviews
8.0/10
1 night
From CAD 107
99
Hotel near Downtown Key West,Key West
A stay at Silver Palms Inn & Historic Homes places you in the heart of Key West, within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. This hotel is 0.7 mi (1 km) from Florida Keys Beaches and 0.7 mi (1.2 km) from South Beach.
Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a television in a common area.
A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM.
Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage.
Make yourself at home in one of the 50 individually furnished guestrooms, featuring refrigerators and LCD televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Complimentary wired and wireless internet access keeps you connected, while iPod docking stations help you enjoy your music in the comfort of your room. Bathrooms have showers and hair dryers.
"The second time I came to Key West, the southernmost town in the United States, the hotel was not in the center of the old town, but it was quiet in the middle of the noisy, it was convenient to go anywhere, the breakfast was simple, but the room was very comfortable, and the former residence of Hemingway was worth seeing."
Very Good
116 reviews
8.9/10
1 night
From CAD 146
99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar
Great
107 reviews
9.0/10
1 night
From CAD 228
99+
Hotels in Monroe County
Featured facilities: Exclusive Beach Area, Bar, Spa
Great
105 reviews
9.0/10
1 night
From CAD 382
99+
Very Good
115 reviews
8.6/10
1 night
From CAD 231
99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar, Fitness Room
Great
100 reviews
9.2/10
1 night
From CAD 393
99+
Hotel near Downtown Key West,Key West
Featured facilities: Exclusive Beach Area, Bar, Spa
Very Good
109 reviews
8.9/10
1 night
From CAD 266
99+
Very Good
103 reviews
8.4/10
1 night
From CAD 128
99+
Very Good
103 reviews
8.7/10
1 night
From CAD 294
99+
Very Good
121 reviews
8.4/10
1 night
From CAD 193
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.
9.1/10
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.
9.1/10
Great
LLuengoRUPGreat trip! We enjoyed it a lot! Great service, we love our room (ocean front) the only issue that we had is that we didn’t have access to internet through wifi
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:CAD 401
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.
8.4/10
Very Good
GGuest UserWe 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.
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:CAD 359
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 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).
7.7/10
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 🌴.
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, Havana Cabana at Key West (from CAD 208) , Parrot Key Hotel & Villas (from CAD 187) and Hampton Inn Key Largo (from CAD 169) 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 CAD 240) 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 CAD 795 on weekdays and CAD 1,101 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 CAD 275), Isla Bella Beach Resort & Spa - Florida Keys (from CAD 361) and Casa Marina Key West, Curio Collection by Hilton (from CAD 206) are popular choices.
Monroe County Hotels with Pools Information
| Total properties | 484 |
|---|---|
| Number of reviews | 16,182 |
| Highest price | CAD 3,000 |
| Lowest price | CAD 216 |
| Weekday Avg. Price | CAD 795 |
| Weekend Avg. Price | CAD 1,101 |