
Vacation rentals with a pool in Key Colony Beach
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Top-rated rentals with a pool in Key Colony Beach
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Popular amenities for Key Colony Beach rentals with a pool
House rentals with a pool

#7 Waterfront 4Bed 3Bath Pool Home
Location, location, location! Great views, nice pool area, dock space if needed. Walkable to several resorts and turtle sanctuary.

Oceanfront mermaid house pool and dock
Greg's place was amazing! I loved being outside, sitting by the water, and looking out at the beautiful view. It is very quiet and peaceful, you feel like you are the only people around. We loved looking for sealife from the dock, and watching the boats go by the canal. The living room was comfortable and clean, and made a cozy place to enjoy the evenings. It was especially nice to have both bedrooms with their own ensuite bathrooms, and suited our two couples perfectly. I would stay here again in a heartbeat!

Waterfront House - 30' Dock & Pool at Cabana Club
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!!

Waterfront Private Home w/Pool-Family&Pet Friendly
This was an awesome home for our family of 4 + dog. We felt right at home for the week! The pool was perfectly warm, and the kids had so much fun playing by the dock. We rented a pontoon boat and were able to dock it easily. Honestly, we hardly used the other amenities in the home because the weather was so nice, but if it rained we probably would have loved the game room too! Overall this was a great home for our family. The neighborhood isn’t super walkable, but the grocery store was just down a little footpath, allowing us to walk to get groceries as needed. Loved this!

Waterfront home w/pool, dock & close to beach
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!

Get Hooked private pool and dock
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!

Marathon 3BR Canal Pool Spa Special WK May 4-11
Great peaceful place to stay. We saw manatees, tarpon and many other species in the canal. Also had some short visits from different types of lizards and iguanas. The pool and hot tub were amazing everyone in our group enjoyed them. The dock was a great place to keep our rental boat. I would 100% come back.

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

2 Bedroom Oceanfront Complex Heated Pool KCB
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!

REEL HIP-NEW & Fun-40' Slip-Private Ramp-Kayaks-He
Angela’s space was neat, clean and well stocked. When we had questions, she answered immediately. When we couldn’t find a can opener she quickly brought us a new one and even included a sweet treat! We couldn’t be happier with our stay. Thanks Angela!!

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

*NEW* Kokomo Views-Pool/Beach
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!

Den Suite Two Balconies- Islamorada
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.

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!

Just a Few Friends - Ocean View and Bring your Boa
Jonelle was very responsive and helpful! Condo is spacious, clean, and full of kitchen ware. Pool is clean and quiet for when we were there. The location is on the south side of the island so restaurants and shops are a drive. Bedding was clean and comfortable. We would definitely consider staying here again!

Sombrero Beach Tropical Getaway
Beautiful place! Phil was a very gracious host. He accommodated us as we arrived a day early to the keys and we were very thankful! This a cute place & has everything you need!
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
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- Everglades National Park
- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Calusa Beach & Loggerhead Beach
- Cannon Beach
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- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Sea Oats Beach
- Theater of the Sea
- Sugarloaf Beach
- Keys' Meads
- Horseshoe Beach
- Long Key State Park