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Vacation rentals with a pool in Key Colony Beach

Find and book unique homes with a pool on Airbnb

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Popular amenities for Key Colony Beach rentals with a pool

House rentals with a pool

Superhost
A private balcony is furnished with a glass-top table and woven chairs, offering a serene view of palm trees and a sandy beach area. The calm water reflects a clear sky, creating a peaceful atmosphere for relaxation.
Home in Marathon
4.69 out of 5 average rating, 16 reviews

#7 Waterfront 4Bed 3Bath Pool Home

CarolRating, 5 stars11 months ago
Location, location, location! Great views, nice pool area, dock space if needed. Walkable to several resorts and turtle sanctuary.
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!!
Top guest favorite
A private pool is surrounded by a paved patio, featuring lounge chairs and a small table. Lush tropical plants provide a natural backdrop. In the distance, a boat dock is visible along with outdoor dining furniture and an umbrella. Soft lighting enhances the inviting outdoor space.
Home in Marathon
5 out of 5 average rating, 14 reviews

Waterfront home w/pool, dock & close to beach

LaurenRating, 5 stars1 month ago
We did a couples’ trip with our three toddlers and had a wonderful stay at Ruth’s place! We had everything we needed and the location was awesome - close to beautiful Sombrero beach, restaurants, nightlife and had a dock where we could dock our rental boat. Would come back in a heartbeat!
Superhost
An expansive outdoor area showcases a clear swimming pool surrounded by a spacious deck. Several lounge chairs and dining tables are situated under the shade of a covered porch. The property features a light-colored exterior and decorative wall art depicting marine life.
Home in Marathon
5 out of 5 average rating, 17 reviews

Grouper House, Lux 4BR, 6BA home w/ pool, dock and

MartinRating, 5 stars3 weeks ago
The Grouper house was fabulous. I stayed there with my wife and kids for a week. Everything about this place was top notch. From booking to check in and check out. Her staff is nothing short of superb. Sean makes sure every need or question is answered promptly. The best place I have ever stayed. Highly recommend.
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
This aerial view captures a canal front home, showcasing two private pools on the lawn and a dock for boat access. The surrounding greenery complements the spacious outdoor areas, while the coastal setting is highlighted by the water's edge.
Home in Marathon
4.95 out of 5 average rating, 21 reviews

Get Hooked private pool and dock

LynnRating, 5 stars1 week ago
We recently had the pleasure of staying at a fantastic vacation rental, and it exceeded all our expectations! The house was comfortable, spacious, and perfectly equipped for a peaceful and relaxing stay. One of the highlights was the location—just a short and scenic walk to the beach, making it easy to enjoy the sound of the waves and the coastal vibe. We were also treated to the most beautiful sunrises each morning, a sight that truly made the experience unforgettable. The home was spotlessly clean, with thoughtful details that made us feel at ease. And Sheri, the host, was incredibly friendly and welcoming, ensuring every part of our stay was smooth and enjoyable. Her kindness added an individualized touch to the experience. If you’re looking for a perfect getaway with stunning views, a cozy atmosphere, and a host who genuinely cares, this place is absolutely worth considering!
Guest favorite
A private backyard features a newly renovated pool and spa combo, surrounded by a concrete patio. The stilted house above is complemented by a spacious screened-in porch with teal seating. Lush greenery enhances the tropical ambiance of the outdoor space.
Home in Marathon
4.97 out of 5 average rating, 34 reviews

Marathon 3BR Canal Pool Spa Special WK May 4-11

JenRating, 5 stars2 months ago
We had an amazing week at this beautiful home in Marathon! The property was impeccably clean, spacious, and thoughtfully designed with everything we needed for a comfortable stay. The location was perfect—close to local attractions, great restaurants, and great location on the canal. The host was incredibly welcoming and responsive, making sure every detail of our stay was seamless. Whether relaxing at the house or exploring the area, this was the ideal getaway spot. We would absolutely stay here again and highly recommend it to anyone visiting the Keys!
Guest favorite
An outdoor space features a large swimming pool surrounded by a well-maintained lawn. Lounge chairs are arranged nearby, and a dining set is positioned under an umbrella. A gazebo is visible in the background, contributing to the area’s recreational atmosphere.
Home in Marathon
5 out of 5 average rating, 10 reviews

Sunset keys villa w/Den, pool, Firepit &Boat space

MichelleRating, 5 stars3 weeks ago
Everything about Lazaro’s stay was 5 Star!! He was easy and friendly to communicate with and went above and beyond to make our stay a delight. The property itself was perfect. Everything is brand new and it was one of the best stocked places I have stayed, from the decor to the spacious layout to the stocked cabinets. The fully fenced yard was perfect for our dogs who enjoyed it very much. The location is on a quiet street in the heart of Marathon with so much close by. Ideal!! Truly a 5 star stay and highly recommended.

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 stars3 weeks 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
A modern game area features a slate bumper pool table surrounded by turquoise chairs. A wall-mounted dartboard adds to the entertainment options. The adjacent kitchen, equipped with stylish cabinetry and contemporary appliances, is partially visible, providing a seamless flow between activities.
Condo in Marathon
4.92 out of 5 average rating, 12 reviews

REEL HIP-NEW & Fun-40' Slip-Private Ramp-Kayaks-He

RichRating, 5 stars2 weeks ago
We loved our time staying here in Marathon, FL. The condo was spotless, quiet neighbors, and the entire family slept great! We will be coming back to stay here again, thank you Angela!!!
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.
Top guest favorite
The image showcases a clear blue pool surrounded by lounge chairs with bright umbrellas, set against the backdrop of the ocean. A sandy beach extends nearby, with a distant building featuring multiple balconies. Fluffy clouds dot the sunny sky above.
Condo in Marathon
5 out of 5 average rating, 11 reviews

*NEW* Kokomo Views-Pool/Beach

EmilyRating, 5 stars1 month ago
PERFECTION!!! I have so many great things to say about our stay. First, the condo was beautiful and fully stocked. It even had plenty of soap, toiletries, paper products etc to get you started. Yuni was the perfect host and answered all questions and gave clear instructions. The balcony was huge. It was enough for the family to eat and lounge all while enjoying the beach and pool views! Key Colony Beach is a charming community we walked to the sunset multiple nights. My kids aged 10,8,7 did not want to leave. The complex had very friendly retirees and a handful of families with kids. Everyone was super respectful and friendly. The pool was super clean and warm. The beach was groomed each night and the kid had plenty of room to play on the sand and hunt for shells and hermit crabs. Marathon is a great Key to stay on - close to lots of fun activities. We are already planning our next trip and we will definitely rent this condo again! It’s perfect for families!
Superhost
A large outdoor pool glistens under clear blue skies, surrounded by a spacious deck with lounge chairs. Modern low-rise buildings are visible in the background, featuring balconies overlooking the pool area. The inviting water contrasts with the light stone and white structures.
Condo in Islamorada
4.77 out of 5 average rating, 13 reviews

Den Suite Two Balconies- Islamorada

GaurangRating, 5 stars3 weeks ago
Great spot to spend days for vacation. Great service by office staff. They took care of all requests we had in the most friendly manner. The hotel is located right on the water, so views were great. Nice pool and great vibe. Would highly recommend.
Superhost
A spacious heated pool area is surrounded by a patio featuring blue lounge chairs and shaded seating for relaxation. Lush palm trees line the border, and a multi-story condo is visible in the background against a backdrop of partly cloudy skies.
Condo in Marathon
4.95 out of 5 average rating, 40 reviews

2-story condo w/ panoramic bay views and balconies

RickRating, 5 stars1 month ago
What a great find I almost want to say nothing and keep this wonderful place to myself but like all great things the word gets out I hope to come back and do it all over again next year a true wonderful find
Guest favorite
A large, inviting pool is surrounded by tropical palm trees and a well-maintained landscape. Sun loungers are positioned nearby, while the spacious clubhouse is visible in the background, offering a shaded area for relaxation.
Condo in Islamorada
4.93 out of 5 average rating, 27 reviews

Just a Few Friends - Ocean View and Bring your Boa

MonikaRating, 5 stars1 month ago
Great location!We had a fantastic stay,we didn’t want to leave! Beautiful home,clean and comfortable,we had everything we need.We enjoyed the pool daily,the complex nice and friendly community. Jonelle was responded quickly with any questions I had and provided great recommendations on restaurant and activities! Islamorada has always been a special place to us!Would definitely stay again!Thank you!
Superhost
A refreshing swimming pool is visible in the foreground, with clear blue water reflecting sunlight. The poolside tiki bar is shaded by a large roof, featuring a row of wooden bar stools. Tropical palm trees surround the area, creating a relaxed atmosphere.
Condo in Marathon
4.87 out of 5 average rating, 233 reviews

Sombrero Beach Tropical Getaway

RyanRating, 5 stars3 weeks ago
Phil always responded quickly to any questions we had and the place was perfect as a home base to explore the Keys! We had a great time!

Quick stats about vacation rentals with a pool in Key Colony Beach

  • Total rentals

    410 properties

  • Total number of reviews

    14K reviews

  • Family-friendly rentals

    370 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wifi availability

    410 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key Colony Beach
  6. Rentals with pools