Swim-up Rooms & Private Pools in Key West

All of the employees from the hot towel boy to the helpful front desk went out of their way to make sure we had a good experience. I stayed in two different suites and they were both beautiful. I love the beach access room and the pool access room was gorgeous too. The downtown shuttle was easy and the driver was friendly. A++ experience

Loved the room with two king bedrooms, each having their private full size bathroom and also halving a 1/2 bathroom. The pool and pool bar were amazing! We had the best time hanging at the pool in between going into town. The guitar player singing in the afternoon by the pool was a great touch and we really enjoyed his music. Loved the location. Close enough to the airport and all that we wanted to do at the main attractions. Ubers were always available to take us to where we wanted to go and were reasonably priced. When leaving our flight wasn't until 3:00 pm, so front desk offered to put our stuff in a room by the front desk so we could go out and spend our last day doing what we wanted without worrying about our luggage. The bartenders were great!!

Overall a really nice experience. Nice ocean view from the ppol, the rooms were clean and spacious, with easy access to parking garage and pool. Staff was friendly and non-intrusive, and maintenance issues were addressed promptly. The nightly $25 parking fee for the parking garage was excessive considering the cost of the rooms and the distance from all the action in Key West. The pool waiters tried to enforce the no outside food, drinks and coolers rule even though drinks were between $7- $15 a piece, which just angered everyone that was poolside. Due to the everglades wildfires, we left a night early, and brightwild promptly returned the last night's room charge, which was really generous. Overall 4.5 out of 5 stars.

When we arrived at this property, we already felt it was a beautiful place. Not knowing really what we were going into, then we opened up the door to our room. We were amazed, have such a beautiful place that we are going to stay. The pool is beautiful. You get service at the pool. There's the pool bar, there's also the ocean right next to it. Everything you need is in our room. We are truly happy. We had extra days at the end of our trip. And we chose to come back and spend a second 4 days here, instead of somewhere new it was that good.

I recently stayed at this hotel and was impressed by how beautiful all the areas were – from the well-maintained grounds to the elegant interiors. The overall atmosphere was relaxing and enjoyable. However, the pool area and bar could use some improvement. Both seemed understaffed during my stay, which led to delays in service and made it hard to fully enjoy those amenities. With a few more employees, the experience would be much smoother. Overall, it's a lovely place with great potential. I’d definitely return, especially if service at the pool and bar improves.

The private pool, & public roof pool/bar makes this resort stand-out! Very friendly & helpful staff that took immaculate care of our room/pool multiple times a day! Made for a phenomenal honeymoon get away!

The staff was so friendly, the private pool was wonderful and we had a fantastic time at the roof top bar and pool. We can’t wait to come back!!!

Location, rooftop pool, private plunge pool.

Great room, nice private pool, beautiful and relaxing rooftop pool, lush landscaping, AMAZING service by everyone working there!

The private pool attached to our suite was great, the courtyard at the hotel was really nice and the hotel staff was very freindly and pleasant. We really enjoyed our stay here and will stay here again when we return to Key West without our children.

I loved the pool access room. We spent the morning in the pool after eating breakfast on the patio and it was really nice.

First time we stayed the Perry Hotel when we travel to Key West again definitely choose to stay again. Staff was friendly location enough far away the back pool like our private pool room so clean and comfortable. They had the dog park love everything about this place. Thank you again! Price really affordable!

We absolutely loved everything about our stay at the Perry Hotel & Marina. From the moment we checked in the process was easy. They welcomed us with a bottle of champagne to celebrate our anniversary. Our room was very nice & roomy. Our view looking over the pool and Marina was perfect! View from our balcony at night was spectacular. Housekeeping staff were friendly. Loved both restaurants. Fernando at Matt’s went above and beyond to make our 40th wedding anniversary special. All the staff at Matt’s were wonderful. Zach at the Salty Oyster was great, he made us feel so welcomed! Loved the pool, met so many nice people. Loved that we could order food & fun drinks poolside. Arthur was very friendly & helpful on places to explore while we rented a golf cart during our stay. It was so fun driving it Oceanside to downtown Key West. Johnny, the concierge was super helpful when we rented a golf cart and our schooner sunset cruise- which was amazing.

our room was clean and the view of the marina was perfect. the pool was great, as was the pool bar. the service was kind and fast. the pool itself was warmed and clean. my wife and I spent a few hours a day lounging.

The location of the Perry hotel is great if you want explore Key West but stay somewhat outside of the very busy areas in downtown. The Perry team was warm and welcoming. Our room was clean, very spacious and with a nice view on palm trees, the pool and overlooking the marina next to the hotel. For our room the pictures on Booking.com were real. Also a gym is available which was clean and provides all the essential stuff. At the pool we never had an issue to find plenty of free deck-chairs and one day there was even a live band playing. A shuttle bus to Key West downtown was available but we did not use it. Parking is also available but comes at an extra fee. Breakfast was not included, but this was no issue for us.

Excellent location! Half a block off Duval. Auxillary off-street parking available first-come-first served at a cost of $25. Super friendly staff, very accommodating. Our room was the smallest I've ever stayed in with a shared bath, but we only slept and showered there anyways. Nice continental breakfast, cold a/c, quaint accomodations. Nice, private backyard pool area that is open 24 hours. Will definitely stay here again, but will upgrade to a second floor room or private pool house with a private bath.

Over all we r happy customers.We did enjoy our room 12, next to the pool(guest house). There was something wrong with our bed, it was a drop in the ocean compare to fun what we have had. Wonderful pool, warm water in it. Quite house .Clean.Nice decoration around the pool. Amazing location!!!!

Wonderful, whacky, just a perfect Key West hotel! great welcome, lovely breakfast, pool and lobby honesty bars, pool towels (and sunscreen) fruit always avaiable in lobby. the ladies were just brilliant, great recommendations from them.Perfect location too.

WOW....don't hesitate staying here....we were in the height of Covid19...and this place had all the protections in place. Now we did not have maid service everyday...but that was understandable.....all we had to do is ask for clean towels and it was granted. Starting withbreakfast..wow....hard boiled eggs, ham, salami, cheese, french toast, yogurt, granola, bagels coffee, orange juice....NOT just a continental breakfast...and it was served because of Covid. In the afternoon around 330...we had complimentary wine....hanging out near the pool was relaxing....and during wine time, she delivered it to us! Now that is service. We did not hear/see any ghosts..and that was ok with me. The room was comfortable....if you looking for a modern hotel room, don't look here...this is over 100 yr old house....if you want quaint, ambiance, and great service.....Marrero's is your choice. What made it very special is the two ladies that service the front desk....hospitality and welcoming....thanks for a great stay!

I spent two nights at this beautiful historic B&B mansion with a friend. We were so thrilled with the grounds, the home, the pool area and the staff. Wine Happy hour everyday at 3:30, a beautifully setup continental breakfast each morning, taken on the viranda, if so desired, and so conveniently located to Duval street, that you don't need transportation to enjoy the action. Our room was quaint and very small ( our choice to make our budget work), but have no complaints about it, really. I rather enjoyed the loft bed! Our stay was a real joy, and we would definitely stay there again. The 21 and over requirement for staying there was a plus, lending itself to a relaxing, quiet experience! A

Hotel was so welcoming & helpful (Peter). We chose a deluxe king room with pool view and it was perfect for us. Parking is free with a small but adequate breakfast included. Nice pool area where you can relax, eat breakfast (with omlettes cooked poolside). Walking distance to all attractions, but if you wanted to use the free "loop bus", there is a stop round the corner.

Where do I start? I typically stay at the big chain hotels, but they were so pricey in Key West that I opted to try the Silver Palms Inn. I was pleasantly surprised by everything about this place; what a gem! The property is well maintained and very clean. The rooms are large, clean, comfortable with comfortable beds. The (saltwater) pool area is the perfect refuge after a long day of walking the streets of Key West. Best of all was the daily omelette served poolside for breakfast. Hot, fresh and delicious breakfast everyday. I loved staying here. Oh, and don't forget free parking on site, a huge perk on Key West.

We love everything about Silver Palms. Second year staying with them and we will definitely be back! Location is perfect, staff is so friendly and attentive. Comfy beds and view of the pool from our balcony. The continental breakfast, including an omelet station, is a great way to start the day. We love relaxing by the saltwater pool before heading out for the night. Bicycle rentals available on site. Scooter and golf cart rentals across the street. This is a perfect, boutique hotel, close enough to everything!

The entire staff was very friendly, always smiling. They were constantly cleaning something, even the tops of the exposed water pipes in the parking garage. Breakfast was very good, never running out of a particular item, like often happens at other hotels. Choice of omelets was a plus to the continental breakfast. We were never more than a 5 minute Uber ride from any of the attractions we visited. Very nice pool and pool deck. Ice water available 24 hours. We would definitely stay again.

the room was clean and the bed and pillows were comfortable. We had everything we needed in the room, microwave, fridge, blow dryers. the breakfast was a continental breakfast but they also had a great omelet station. the pool was very clean . Siver Palms as a whole was very clean. they cleaned the pool and area every day. they wiped all hand rails everyday. People were excellent. I would stay again.

I loved Ibis Bay resort. Everyone from the front desk to maintenance was very nice and friendly. Only thing that was mean and with the attitude was Lexi, the parrot. Lol. Everything was very clean and very highly maintained. Rooms are little old, they are beautiful don’t get me wrong, but they could use little renovation. Our room went out on the beach, total pleasure. I could sit there the whole time if you let me. Pool side was beautiful, with the pool bar. I swear I became an alcoholic. I tried every cocktail on the menu twice, lol. Absolutely delicious! Kids had lot of fun too! Hammocks everywhere were very comfortable for afternoon naps for my 2 year old. My son enjoyed shark feedings very much. And the foooood at the Stoned crab restaurant! Woow! Everything that we ordered was absolutely delicious! So fresh and tasty. Great presentation and very good portions. Prices are also reasonable. They have a “Life is too short bus” shuttle that takes you to the city and brings you back. We didn’t have to rent a car, you don’t really need a car with the shuttle service. If I ever go back to Key west, that’s where I’m staying.

The whole place was a great experience for the family. They have a couple of fun Macaws that you can interact with. They have some turtles and they also have shark feedings. We didn’t have time in our vacation plan to take advantage of the jet ski, kayak rentals, or the Life is Too Short Bus, but those looked really fun. I loved that our room had a bayside view with lounge chairs and a hammock on the palm trees. The pool with the poolside bar was really nice too!

Super friendly staff. Made check in a breeze. It’s an older but, super cute resort. Complimentary breakfast and coffee was an added bonus. Pool was clean and welcoming. Open air restaurant and pool bar was great and loved that the kept the vacation vibe with music. Will be returning!

Really lovely room with beachy decor. Very clean but we did not get maid service even after asking for it. The patio was very nice but upon sitting out with snacks we were immediately visited by iguanas including one over 3 ft. Long. Pool was very nice. Enjoyed being able to sit at bar and have lunch by the pool. Overall a good experience.

This property needs an upgrade for the price of a bayside room. The pool needs lights in the pool for kids to swim at night. If I were to go back I wouldn’t pick this hotel.

Very convenient location yet very private. Pool was right off room. Great little bar area and continental breakfast was very good Beautiful grounds

Beautiful oasis in the heart of Old Town Key West. The staff was friendly and helpful, from the front desk at check in to the bartenders, to the pool and custodial staff. The three pools form hubs from which the rooms and amenities branch off. Staying in the Annex was a smart choice as we could retreat there and be just off a pool or wander not too far back to one of the two main pools by the bar and lobby. My only critique is that the bed and pillows were too soft for my liking and they didn't advertise options to swap them out. Being a bit creaky on vacation (even without all the walking through town) isn't that pleasant. Thankfully a float in the pool and ocean helps. But the AC going on and off through the night was also frustrating. It was very loud for a fairly luxury place. Replacing it with something quieter would go a long long way. Otherwise, I'd come back next time we head to the Keys!

This place is so quaint and adorable. It’s got an old Florida feel to you. The rooms were perfect. Our room was right in front of one of the pools. We had the pool to ourselves for two days. The pool was 89 degrees! Each little bungalow was cuter than the next. Our desk clerk (Richard). Was so nice and helpful checking in and out. The breakfast was pretty good. The breakfast bar was nestled in between the bungalows. It was just so perfect! The location was also awesome. Close enough to walk to everything but not so close that you heard the late night parties! I highly recommend Winslows Bungalow’s! We will return.

Our stay here was magical! We arrived around midnight due to flight issues and were met by a friendly Manager to check us in. The grounds are gorgeous and there's little areas all over the property to tuck yourself away and read a book or enjoy a drink. We stayed in the Annex across the street. It was so cute and we had our own little pool all to ourselves the entire time. It's a very quick walk to the "main" pool by the bar and restaurant. The complimentary buffet for breakfast was wonderful and the drinks at the bar were delicious! I really appreciated the purified water stations for refilling our bottles. The location of the Winslow is hard to beat. Your right smack dab in the middle and can be anywhere on the island in 5 minutes to 15 minutes via bike. Definitely rent a bike, it's so much fun to cruise around!

We had a five star experience at Winslow’s bungalows. Great location a few blocks from Duval street but it was very peaceful and quiet onsite. The rooms are situated in multiple buildings around the site and they have three pools and a bar. The grounds are lush and well maintained. We were in the annex building across Elizabeth st. but still close to all amenities plus our pool felt very private. Rooms were nicely appointed. The onsite bar was a plus as was the continental breakfast. All the staff were very friendly and informative. They provide onsite parking for a fee which was not excessive.

Great key west resort. We stayed in MA1 and had no complaints about the room. Pretty quiet at night as well. The private porch was fantastic. Great complimentary breakfast. I kept going for the bagels and hard boiled eggs. We got one free drink which was also nice. Assortment of pools to choose from. My ONLY complaint is that it was warm during our trip and they still had the pool heaters on. I asked the front desk if they could turn it down and they said no. However, another guest at the main pool asked the pool maintenance man and he was able to do it. I don’t know why it couldn’t have been for the others. Regardless, loved our stay and we’d definitely come back. Looking forward to it!

We just returned home from our 3rd stay at the Simonton. Hands down the staff here are the best. From Jonathan at the front desk who found me a yoga mat to use in my room during our stay right down to every housekeeping staff member or groundskeeping crew. Everyone says hello whenever you pass them. The housekeepers inquire as to if you need anything specific (towels, always towels lol). Which is great when you don’t need the entire room serviced. We love the historic and rustic nature of this hotel. We’ve found our favorite room that we’ve stayed in twice. With all there is to do in Key West it can be difficult to take advantage of all the included amenities they have. From yoga by the pool, your complimentary drink, the various sip and paints, or the food tour. They offer it all. And of course, 4 pools on the property! They’re small but rarely crowded. And if one is there are 3 more. The black bottom pool is definitely our favorite. Great included breakfast as well. Nothing fancy but lets you ease into the day perfectly. And don’t forget the cutest hotel cat. Thank you to Jonathan and rest of the Simonton family for being so amazing that we come back year after year. See you in 2026!

The walkway just past the front gate is magical. Full of lush trees, plants, and orchids. At night it is lit with beautiful lighting. The heated black bottom pool was our favorite and seemed secluded as there are not a ton of guests and there are 4 pools to choose from. The staff was very friendly and helpful. Lots of complimentary breakfast options, you put in an order, and they deliver it to your outdoor table by the pool or on the mansion porch. This was really the getaway my husband and I needed to decompress, recharge, and soak up the tropics.

This was our second year at the simonton court. There are so many things about this location we love, I don’t know where to start. They are accommodating, polite, the grounds are beautiful! Complimentary breakfast by the pool is a relaxing way to start the day. The location is close to all the action, but set remotely for quiet privacy. I love all the pools at their different temperatures and the 24 hour accessibility. The concierge will call you a cab, get you discount on a golf cart, and bring anything you need to your room. You can even use one of their bikes for a day to explore the island. Thank you to everyone that made our vacation there wonderful !!!❤️

Where do I begin!? First, the staff at Simonton Court are wonderful - they are caring, kind, and so accommodating to all guests. Specifically, Jonathan and Violet really went out of their way to make our baby moon the most memorable trip! Second, the hotel itself is so beautiful! We loved the tranquil setting, the pools, and the lush greenery. Third, the breakfast is fantastic! It was so peaceful to come to the beautiful poolside patio every morning to eat a big breakfast. I would HIGHLY recommend Simonton Court to anyone traveling to Key West for the most peaceful and relaxing stay:-)

location was perfect, everything in walking distance private pool and hot tub free drinks at happy hour free snacks and breakfast cleanliness and functionality the staff has thought of it ALL and they are SO personable

The host/staff were extremely friendly and accommodating to our unique arrival needs. The property has a small private boutique hotel feel. The room is very cozy and the overall property is in a calm "Key West" decor style. The grounds and gardens were VERY beautiful. The pool and hot tub location are perfect. Having the hot tub warm the pool in cooler months is a must. A very nice option. Also, the properties trees and landscape provide the perfect amount of shade and sun over the pool. Oh and do not miss that they offer an i sane amount of amenities, breakfast, snacks, coffee, and a fun happy hour with a FULL bar with Kevin. Kevin greats you with a warm smile and by the time you check-out you feel like you have made a new friend. I can tell they put a lot of heart into making guests stay in Key West fun, comfortable and memorable.

This place is exceptional, very clean, cozy and centrally located- just perfect for our stay in Key West. The hosts warmly welcomed us and were extremely friendly and helpful throughout our stay. On top of anything else we very much appreciated the availability of comfortable pool towels, a really good washing machine & dryer and much more little things that were even complimentary to our surprise. The pool and hot tub are very nice too and are open until 10pm. We can highly recommend this facility and will definitely return when coming back to Key West.

The pool deck was quiet and secluded and right off our room. The close location to the action of Duval St yet a quiet side street provided the best of both worlds. The hot tub at night was a very nice way to end the day. Little things like cold water at the pool, happy hour each evening, complementary laundry machines added to the positive experience.

Hubby and I visited Key West for the 4th of July/our anniversary and KWV is a GEM! Upon reserving the room we instantly received a text thanking us for our reservation and checking in if we needed parking/estimated arrival time. Fast forward to the day of check-in, Kevin (one of the owners) met us in the parking lot to give us our parking pass, checked us in and gave us the run down of all of their amenities and all I can say is WOW! They offer FREE bottle of wine with check-in, FREE daily breakfast (coffee, muffins, fruit, waffles, yogurt, hardboiled eggs, etc), FREE snacks & drinks in office from 11-3pm daily, FREE happy hour with a full bar from 4-5pm daily (with specialty shot of the day) plus on-site laundry, beach towels, a beautiful pool/hot tub, ice chest full of cold waters and rooms that are spacious, clean and comfortable. I almost hesitate to write this review because this place is so fabulous and I don't want to let the secret out! Overall I can't recommend this place enough and will be back as soon as we can!

I loved waking up and having coffee on the deck and watching the manatees swim up to us. Very clean facilties, staff is great and there is a ship store for snacks, coffee and sundries. The restaraunt on-site serves excellent fresh seafood with a daily catch special that fills you up. Highly reccomend.

This is a Must Do Adventure Stay for Key West. Staying on a House Boat is truly the way to enjoy the area. This house boat can sleep up to 6 adults, or a whole passel of kids. The loft area is a fun addition for the kids to sleep. Kitchen includes everything you need, from microwave, stove, full size refrigerator, coffee maker and toaster. Perfect for a family on a budget. The beds were very comfortable and the bathroom was large and spacious. Yes, you are using a boat toilet, but it is just like a normal one, except you use the foot pedal and keep a small amount of water in the bowl when you are done. Just like RV living. There is a beautiful dock on the back of the houseboat to watch the manatees and other wild life. There is a store and dining on property. Best yet is you can rent a boat, rent a kayak, jet ski or paddle board. You are only 4 miles from Duval Street in Key West, and there are rental golf carts near by. Highly Recommend this Stay.

The house boat was perfect for us. We only had three days down in the keys so everything had to work effectively and efficiently. Property was clean, location was excellent, the marina is a great place to stay with super friendly staff. We were 5 so it was a slight squeeze but the boat managed it well. Watching the massive tarpon top on the marina in the evening and the nurse sharks waiting for fishermen to clean their catch was amazing. José was on it. First night we arrived we noticed we were a couple of sheets short to make up the sofa bed, within minutes he’d come from his home with what we needed and extras at 8pm at night! From that moment we knew we’d picked the right place. Matt (I think? Sorry if I’ve given you the wrong name🤦🏻‍♂️) was in the marina office, always helpful full of knowledge, checked weather reports for us, a decent bloke. The staff are all local, some even fisherman, so their knowledge of reef, Sand bars, good spots and bad is amazing.

What we like about the lodge the most was that I can come and go freely with no front desk awkwardness.. We felt like we were enjoying the best of Key West at Aqua Lodge. I had a flat tire, and it was convenient to have a tire shop right next door. Not only did they service electric scooters, but they also service my rental car as well at a very decent price.Hurricane Hole was the best restaurant in Key West, and we were there for a week. We saw great marine wildlife, kayaking, and a boat ride around Key West. The house boat itself was a dream experience. Enough space for 20, but remember only one bathroom. The AC kept us cool in the middle of July with 110 degrees outside.The patio deck with that rain, 👌 awesome. Morning and evening rain, romantic and peaceful. We will definitely be back. Stay safe, Aqua Lodge 🙏

This is a super location on a small marina just a short hop from downtown Key West. We loved the quirky nature of the Aqualodge, being on the water, and part of the working marina. The lodge itself has what one needs for a few days stay and kayak and bike rental is within a 2 minute walk as is a good bar/restaurant. What made it a 10+ for us was the wildlife--the afternoon we arrived a group of seven manatees drifted through the marina and past our lodge. This alone made it our new favorite place to stay. They returned every late afternoon to glide around for a few minutes.Towels were plentiful, the staff were available and helpful. Parking is free but can be hard to find when there are a lot of people in for charters and trips. We will return!