
Holiday rentals with a pool in Sunset Key
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Top-rated rentals with a pool in Sunset Key
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Popular amenities for Sunset Key rentals with a pool
House rentals with a pool
Guest favourite

Home in Marathon
5 out of 5 average rating, 9 reviewsSandbox
CretiaRating, 5 stars3 days ago
⭐️⭐️⭐️⭐️⭐️ Absolute Paradise in the Heart of the Keys! Our stay at this vacation house in Marathon was nothing short of incredible. From the moment we arrived, we felt like we had found our own private slice of paradise. The house was spotless, beautifully decorated, and had all the comforts of home—plus the added bonus of breathtaking ocean views and island vibes. The location couldn’t have been better. Tucked away in a peaceful part of Marathon, we were just minutes from everything—the beach, boat rentals, amazing restaurants, and the iconic Seven Mile Bridge. The property itself was incredibly well-equipped: a fully stocked kitchen, super comfortable beds, high-speed WiFi. What really made this place stand out was the outdoor space. The private dock was perfect for fishing and sunset cocktails, and the pool made it hard to ever want to leave. We even spotted dolphins just off the dock one morning—unreal! The hosts were friendly, responsive, and went out of their way to make sure we
Top Guest favourite

Home in Marathon
4.99 out of 5 average rating, 137 reviewsCancellation Deal: 08/02 thru 08/09
KevinRating, 5 stars1 week ago
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie
Guest favourite

Home in Cudjoe Key
4.97 out of 5 average rating, 159 reviewsCudjoe Key Home with a View
RobRating, 5 stars3 weeks ago
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!
Guest favourite

Home in Key West
4.97 out of 5 average rating, 66 reviewsGorgeous Romantic Private Villa, Steps from Duval!
CliffordRating, 5 stars2 months ago
We had a fantastic stay at Villa Serendipity. Great location right off Duval Street within walking distance to everything. Private and secluded. The pool is small and shared with 12 units, but it was nice. The courtyard is welcoming and peaceful. Bed was very comfortable. Well appointed kitchen; having the ice machine was great! Hosts communicate well. Parking was tight but once we got a spot we didn’t move the car for the rest of the trip. Overall had a great time at this excellent spot in Key West!
Guest favourite

Home in Marathon
4.89 out of 5 average rating, 66 reviewsBeautiful Beachfront Villa w/ Pool/Tiki/Dock
RobinRating, 5 stars2 weeks ago
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️
Guest favourite

Home in Key West
4.94 out of 5 average rating, 103 reviewsParadise found
JenniferRating, 5 stars3 weeks ago
The house was clean and a great option for traveling as a large group. It was away from the bustle of Key West, but still easy to get around, and the restaurants nearby are delicious.
Superhost

Home in Cudjoe Key
4.83 out of 5 average rating, 264 reviewsOCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
AlexRating, 5 stars1 month ago
The house was exactly as pictured and in a very peaceful community. The beds were comfortable, as was the couch (two of our group opted to sleep on the couch itself instead of pulling out the sleeper sofa, and said it was pretty comfy!). Several of our group enjoyed using the bikes at night, and while we didn’t use the kayaks, it’s nice they were available. We didn’t get to do everything we hoped to do on our trip to Keys, but we plan to stay here again someday when we come back!
Superhost

Home in Marathon
4.67 out of 5 average rating, 12 reviewsP76 - Meticulous 2 bed, 2 bath home with stunning
FreidaRating, 5 stars4 months ago
The views are breathtaking!! We loved every minute we spent here. Will absolutely stay again if it’s still available.
Condo rentals with a pool
Superhost

Condo in Key West
4.5 out of 5 average rating, 10 reviewsMagical Sunrises on the Atlantic, Upgraded Condo &
CherylRating, 5 stars1 month ago
I wanted a relaxing getaway for the weekend and this was it! Can’t say how much we enjoyed our stay! We had our 21y/o twins with us. Condo was clean & spacious. It had what we needed to make breakfast each morning. Location is everything and this provided the quiet you want on vacation while still being close to the activity. We spent mornings touring Key West. Each afternoon we came back to sit by the pool and relax until dinner. We plan to return next winter for another stay.
Superhost

Condo in Key West
5 out of 5 average rating, 6 reviewsGalleon Resort - Walk to Duval & Mallory Square!
PatriciaRating, 5 stars5 months ago
Incredible view! Place was clean and what we expected. Gorgeous unit right on the water. Watching the boats go by was so relaxing. Tiki bar right below us was convenient if we wanted a drink while relaxing. Had a small problem with the dryer and they came to fix it within the hour, so I was more than satisfied with upkeep. Walk to restaurants and hot spots was easy. Great Irish pub a block away (Celtic Conch). Unit is convenient for any type of boating excursion you would like to book as the boardwalk/marina is right there. Chris, our host, was very responsive to any questions we had and very helpful in booking arrangements. We did not have recommendation questions for him, as we’ve been to key west a number of times and have friends who live there, but I’m sure based on the dealings we had with him, he’d be happy to help. One note, this is a timeshare community. I was worried we’d be hounded. We were not.
Superhost

Condo in Key West
4.92 out of 5 average rating, 13 reviewsAndy’s Attic | Budget-Friendly!
ChristinaRating, 5 stars3 weeks ago
The room was very small, but was exactly as described. It required a bit of creativity to unpack, but once we figured out how to set ourselves up it was perfect. Perfect location and accommodations. Staff was super responsive & helpful with our random questions. Definitely encourage visitors to rent bicycles to get around!
Guest favourite

Condo in Key West
4.78 out of 5 average rating, 299 reviewsAffordable Beachfront Luxury Condo Sleeps 6
SharonRating, 5 stars1 month ago
Traci’s condo was great in every way! Everything was very clean and the view was amazing. We could enjoy watching the turquoise water and swaying palm trees from almost every room – both bedrooms, living room, kitchen, dining area, or relaxing on the large balcony. Some of the furniture is different in the photos, but my group agrees it is even better now than what you see. Having our own parking space in the garage was much appreciated, too. Traci responded quickly; clear check-in instructions. We would definitely stay here again.
Superhost

Condo in Key West
5 out of 5 average rating, 6 reviewsFair Winds @ The Foundry~ Frolic On Duval St
KathleenRating, 5 stars9 months ago
Comfortable, spacious space with all we needed to feel right at home. We loved the neighborhood! Peaceful, beautiful and quiet, yet so close to any restaurant, shop, museum or beach we wanted to go to. We ditched the rental car and walked or rode bikes to get around. The rental is beautiful with floor to ceiling windows to let afternoon sunshine in as well as the garden views from the front porch. The artwork and decor brought in the island vibe … very cozy and carefree. And the Historic Key West Vacation Rental staff were great to work with … responsive and professional. This vacation rental checked all the boxes for us!!
Superhost

Condo in Key West
4.89 out of 5 average rating, 27 reviewsNew Listing! Key Lime Paradise/Condo
StevenRating, 5 stars1 week ago
We Definitely would stay again if we are in the area. The place was exactly as advertised and centrally located. we had a nice relaxing time.
Guest favourite

Condo in Key West
4.99 out of 5 average rating, 71 reviewsThe Palms
DavidRating, 5 stars4 days ago
Horrid, horrid, horrid. Now that caught your attention. If you are looking at others...dont. This is the best air bnb you gonna find. It has everything and more!! Fantastic location, great apartment. We really cant say anything bad at all!! We will be back!! Thanks!!
Top Guest favourite

Condo in Key West
5 out of 5 average rating, 32 reviewsEYW Getaway
JesseniaRating, 5 stars1 week ago
We had a great stay! The place was clean, comfortable, and had everything we needed. The location was perfect, and communication with the host was smooth and easy. Would definitely stay here again, highly recommended!
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