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Vacation rentals with a pool in Sunset Key

Find and book unique homes with a pool on Airbnb

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Popular amenities for Sunset Key rentals with a pool

House rentals with a pool

Guest favorite
A serene pool area is surrounded by lush tropical palm trees and vibrant landscaping. Sunlight reflects off the clear water, creating a calming ambiance. Nearby, a white lounge chair is positioned for relaxation, with a life preserver visible on the side.
Home in Key West
4.9 out of 5 average rating, 91 reviews

Gone Coastal

JimRating, 5 stars3 weeks ago
We enjoyed our stay here. It was an out a 20-25 minute drive to Duval so did have to take an Uber everywhere we went since we hadn’t rented a car. Overall it was a very nice place-we just weren’t crazy about the location.
Guest favorite
A large swimming pool is surrounded by palm trees and sun loungers, inviting relaxation. Umbrellas provide shade over seating areas. The water reflects sunlight, enhancing the tranquil atmosphere. In the distance, the ocean can be seen beyond the pool, contributing to the scenic backdrop.
Home in Key Colony Beach
4.94 out of 5 average rating, 49 reviews

Waterfront House - 30' Dock & Pool & Cabana Club

LauraRating, 5 stars3 months ago
We will be back! We loved it! Clean, comfortable with lots of room. We loved being able to keep our boat behind the house and the trailer in the driveway. We loved walking around Keys Colony. The Cabana Club and Sparkys Restaurant were both within walking distance. The kitchen had every gadget you could imagine. The dining table was perfect for dinners and card playing. The beds were comfy. No allergies whatsoever! Thank you so much!!
Superhost
A private pool glistens under the sun, surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. In the background, a tiki palapa with a thatched roof offers shaded seating, complemented by lush tropical foliage and a distant pink house.
Home in Summerland Key
4.88 out of 5 average rating, 34 reviews

Pelico Palms Sunset Suites

TimRating, 5 stars1 week ago
fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!
Guest favorite
A quaint outdoor seating area features a round glass table surrounded by two wicker chairs, each adorned with colorful cushions. A decorative wall panel with a Buddha motif adds an artistic touch, while large windows invite ample natural light into the space.
Home in Key West
5 out of 5 average rating, 23 reviews

Catherine House: A charming Old Town Key West

MichaelRating, 5 stars2 months ago
We thoroughly enjoyed our stay at the Catherine house and it was a perfect location to explore Key West. Beautiful space and well thought out. Perfect for two couples! A welcome retreat when you wanted to get out of the Key West hustle and bustle. We loved our time there!
Guest favorite
Home in Key Colony Beach
4.97 out of 5 average rating, 36 reviews

P23 - New 3 bedroom 2 bath duplex with private po

AndreaRating, 5 stars13 months ago
Our stay was wonderful! Key Colony is a quiet and peaceful community. Our condo was beautifully decorated and had everything we needed for the first couple days. The sheets and towels were soft The beds were very comfortable. We really enjoyed our stay and hope to go back soon again!
Superhost
A private pool area is surrounded by tropical landscaping, featuring lush greenery. Several lounge chairs with blue and white stripes are positioned around the pool, inviting relaxation. Bright sunshine casts light across the tranquil water, enhancing the peaceful outdoor setting.
Home in Key West
5 out of 5 average rating, 9 reviews

Casablanca ~ Fabulous Home w/ Private Pool/Parking

KathleenRating, 5 stars2 months ago
The house is perfect! It’s very clean and has everything you need. The kitchen is fully stocked with plates, glasses, etc. The bathroom had a nice shower and plenty of towels. We love the location! We parked our car and never used it. You can walk everywhere. The backyard is amazing. The pool is beautiful. We swam every day and loved sitting in the yard relaxing. We will be back.
Superhost
Home in Marathon
4.73 out of 5 average rating, 60 reviews

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage

MichelleRating, 5 stars2 weeks ago
We had a great stay. The backyard is absolutely beautiful and feels very peaceful. We were treated to four manatees as well as a nurse shark off the dock over the course of our week here! The pool and spa were great and as advertised. Heather’s home is incredibly well stocked- more than enough towels for the baths and pool and the kitchen had everything needed for cooking as well as a great dishwasher which was great for vacation. Although we did have some issues with the property after check-in, the property host, Katie, was immediately available and very responsive to our concerns, and we were more than happy with the outcome. Would stay here again.
Superhost
A private pool is surrounded by lounge chairs on a concrete patio. The stilted home features a balcony above, supported by pillars. Lush greenery frames the area, while a bright blue sky adds to the inviting atmosphere.
Home in Marathon
4.82 out of 5 average rating, 17 reviews

Sale! Pool, Hot Tub, Dock & Putting Green!

NicoleRating, 5 stars1 month ago
We had an amazing time! The location is perfect with so many things to do, pool, hot tub, canal, etc. The home was overall beautiful and we loved every second of it!

Condo rentals with a pool

Superhost
The room features two spacious beds with crisp white bedding and decorative pillows. Light-colored walls complement the beach-themed artwork. Plantation shutters allow natural light to filter in, and bedside tables with lamps are positioned between the beds. A ceiling fan enhances comfort in the space.
Condo in Key Colony Beach
4.75 out of 5 average rating, 164 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

RobertRating, 5 stars1 month ago
We had a great time! Awesome community with walkable restaurants and bars. We loved the local beaches. The people at the complex were super nice. Our four boys loved running from the pool to the beach. Everyone we met was very nice. Great instructions and recommendations. Loved it!
Guest favorite
The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.
Condo in Marathon
4.93 out of 5 average rating, 91 reviews

On the water! Marina, Pool, Tiki Bar & Restaurant!

FionaRating, 5 stars3 weeks ago
We loved our stay at the Dapper Dolphin! The space was so clean. Kate has everything there for you - from beach chairs to laundry detergent! This apartment is conveniently located to great restaurants, attractions and Sombrero Beach. You are just a short walk to the pool at Skipjack Resort. They have poolside karaoke on Monday nights which was very fun. Highly recommend booking this place - we miss it already!
Guest favorite
A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.
Condo in Key West
4.97 out of 5 average rating, 73 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

LesleyRating, 5 stars2 weeks ago
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.
Superhost
A resort-style pool area is featured, surrounded by palm trees and lounge chairs. Shade is provided by large umbrellas over the seating. The pool surface reflects the clear blue sky, creating a serene and inviting environment for relaxation.
Condo in Marathon
5 out of 5 average rating, 3 reviews

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants

MichaelneuroRating, 5 stars3 months ago
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.
Superhost
A panoramic view showcases the tranquil ocean, framed by palm trees and lush greenery. The scene captures a clear blue sky and the vibrant color of the water, with the outline of nearby buildings visible in the backdrop.
Condo in Key West
4.73 out of 5 average rating, 94 reviews

Top floor Ocean Views, Spacious 2 Bedroom Condo, V

JudyRating, 5 stars1 month ago
This was our first time in Key West. We wanted to stay a little tucked away from the downtown bustle. The complex is beautiful with great amenities. And it’s close enough to shopping, restaurants and bars! We definitely plan on booking the same place in the future!!
Guest favorite
A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.
Condo in Key West
4.9 out of 5 average rating, 138 reviews

Tropical Escape at Sunrise

RobertaRating, 5 stars2 weeks ago
Eric’s place was lovely, well maintained, nicely appointed, and immaculate. The 3 of us enjoyed the balcony overlooking the pool. Even though the apartment is near the airport we only heard planes twice in the 4 days we were there. There is a convenient little grocery store on the site and excellent BBQ from a food truck near the pool. Eric responded to our questions promptly. Comfy beds, everything worked and we enjoyed our stay. Would stay here again.
Superhost
A serene ocean view is captured, showcasing the calm turquoise waters and distant boats. Lush palm trees frame the scene, while a community pool and sandy beach are visible below, inviting relaxation in a tranquil, tropical setting.
Condo in Key West
4.84 out of 5 average rating, 154 reviews

Anchor Drop modern elegance upgrades throughout vi

SamanthaRating, 5 stars5 months ago
We loved everything about this place. It was super clean and fresh. The bedding was very comfortable and felt expensive. We drank coffee on the balcony every morning watching the ocean. The oceanfront pool area was clean and well taken care of. The unit was stocked and well labeled with all that we would need and more. The garage door opener for inside private parking was amazing. We watched the Tyson fight in the living room on the BIG tv! Had a great vacation. Thank you.
Guest favorite
A spacious balcony view reveals a heated pool surrounded by lounge chairs. Tiki huts are visible nearby, alongside the boat slips and palm trees, set against a clear blue sky, showcasing a relaxing outdoor space for guests.
Condo in Key West
4.88 out of 5 average rating, 147 reviews

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

ErikRating, 5 stars1 week ago
Great Place! Everything was so easy from booking to checking out. Jennifer is very communicative, gives clear instructions and responds in a timely manner. The home is clean, comfy, has a very nice view, and we enjoyed sitting on the balcony and listening to the music from the restaurant down below (don't worry, the music stops at a reasonable hour). The downtown area is close enough for us to ride bikes. Publix grocery store is close by too. If we're ever back in Key West, we wouldn't hesitate to stay here again.

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