Vacation rentals with a pool in Key Colony Beach

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Top-rated rentals with a pool in Key Colony Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.
Home in Key Colony Beach
4.98 out of 5 average rating, 126 reviews

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

Top guest favorite
A serene outdoor space features two wooden lounge chairs positioned on a grassy area beside calm waters. A small table is placed nearby, and a private dock extends towards the water, flanked by lush greenery in the background under a bright blue sky.
Townhouse in Key Colony Beach
5 out of 5 average rating, 12 reviews

Castillo Del Mar- Ocean access from your backyard

Welcome to PARADISE! — perfect for salty families, fishing lovers and beach goers • Prime Location – In Key Colony Beach with access to Cabana Club pool & private beach • Walk to Dining – Steps from Sparky’s Landing & Island Company • Boater’s Paradise – Backyard dockage for boats up to 30 ft • Spacious Kitchen – Family-style layout with 4-person bar top • Boho Dining Room – Perfect for cozy dinners and entertaining • Amenities include washer + dryer, fully stocked kitchen, Cozy Tv Room

Top guest favorite
Townhouse in Key Colony Beach
4.92 out of 5 average rating, 102 reviews

The Palm House in Key Colony Beach, Florida Keys

3/2 Duplex 37.5' dockage on canal in Key Colony Beach. The property's private (fenced in) back patio has a BBQ, couches and dining table/umbrella facing Eastward with morning sunshine and afternoon shade. Property includes usage of the Cabana Club, a large heated/cooled pool, hot tub, Atlantic Ocean beach and drinks/hot food just a 5 minute walk away. The concrete/wood dock has a fish cleaning station, bait freezer, water hose and gated access for the your boat. Welcome back to paradise !

Guest favorite
A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.
Home in Key Colony Beach
4.94 out of 5 average rating, 136 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Top guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 52 reviews

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

Fresh and Clean!! 2 Paddle Boards and 6 Bikes!! Our home is located on the south end of 9th Street, making it an easy walk to Sunset Beach, Key Colony Inn and access to "Members Only" Cabana Club w/ Pool, Beach and Restaurant. We have everything you'll need for a wonderful vacation! Need something special, just ask! The 37.5' dock with plug in, fish cleaning station, water and green underwater fish light will be sure to please any angler and crew! KCB is the GEM of the FL Keys!!

Superhost
Home in Key Colony Beach
4.88 out of 5 average rating, 17 reviews

P27 - Private Beach Access! Pool home with everyth

This beautiful 3 bedroom, 2 bath home located in the very desirable Key Colony Beach, boasts a large open floor plan, private beach access, relaxing tropical vibe, and abundant sunshine! As an all ground level home, guests are always pleased by its ease of access and freedom to spread out and enjoy all this tropical home and grounds have to offer. This home also uniquely offers membership to Key Colony's private Inch Beach. - Maximum Occupancy: 8 guest (6 adults max + 2 children)

Guest favorite
A private beach area is presented with lounge chairs arranged under shaded tiki huts. The clear blue sky reflects off the calm ocean waters, while palm trees provide a touch of greenery. A BBQ grill and picnic table are available for guest use.
Condo in Key Colony Beach
4.9 out of 5 average rating, 210 reviews

Nautical Condo Oceanfront Complex w/ Heated Pool

Beautiful condo in Key Colony Beach oceanfront complex. Condo has one king bed, well-equipped kitchen with full size appliances and everything you need to cook and serve meals. Free, fast, reliable WiFi, SmartTV and free parking. Enjoy stunning views of sunrise from our private beach and sunsets next door at Sunset Park. Heated pool, beach BBQs and tiki huts for guest use. We are centrally located to awesome Keys adventures just a few miles drive from the condo.

Guest favorite
The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.
Condo in Key Colony Beach
4.88 out of 5 average rating, 154 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Guest favorite
A two-story home is set against a backdrop of vibrant greenery, with a private in-ground pool visible in the foreground. A white fence outlines the pool area, while steps lead to a spacious balcony above that overlooks the pool.
Home in Key Colony Beach
4.89 out of 5 average rating, 125 reviews

Pet Friendly Half Duplex Pool Home with Boat Slip

Want a spacious home with private pool and dock? You have found it! On a deep water canal. Enough dock space for a 37' boat. Enjoy your private heated pool or lounge in the shade or sun. Water views from EVERY room (canal in back, pond with fountains in front). Easy walking to restaurants, shops, golf course, park, playground and entertainment. YOU MUST AGREE TO THE CITY'S RULES, IF YOU BOOK. Pool heater optional. $50/night or $250/week

Top guest favorite
A private pool is framed by a well-maintained lawn and patio area. Umbrellas provide shade for seating, while a tranquil canal with boats is visible in the background, enhancing the serene outdoor environment.
Home in Key Colony Beach
5 out of 5 average rating, 95 reviews

“La casa azul” step 3’ to a private pool

Escape to this 2BR/2BA half duplex in Key Colony Beach on a deep-water canal with 37.5’ private dock and fish cleaning station. Enjoy instant access to both ocean and Gulf. Relax in your private heated pool overlooking the canal. Inside offers a bright open living space and fully equipped kitchen for fresh catch meals. Master has king bed and en suite; guest has queen bed. Perfect for boating, fishing, and relaxing in the Florida Keys.

Top guest favorite
The living area features contemporary furnishings and large windows, allowing for bright natural light and views of the waterways. A dining table is positioned beside the seating area. The spacious lanai showcases an outdoor dining setup with a view of the dock and water.
Home in Key Colony Beach
4.95 out of 5 average rating, 133 reviews

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Superhost
An aerial view of a vibrant waterfront neighborhood showcases a pale yellow house surrounded by lush greenery. Nearby, several homes with varying colors and styles line the streets, while a deep canal runs at the back, providing easy waterway access.
Home in Key Colony Beach
4.89 out of 5 average rating, 27 reviews

KeyColony,4 Bedroom, Pool, 40'Dock, Quick Vaca Cut

Canalfront 4BR home in Key Colony Beach with private pool, dock, outdoor kitchen, and quick access to both the ocean and bay via Vaca Cut. Sleeps 8 with 2 king and 2 queen bedrooms. Walk to restaurants, pickleball, golf, and the oceanfront park for sunsets. Ideal for families, boaters, fishermen, and laid-back Keys weeks.

Popular amenities for Key Colony Beach rentals with a pool

When is the best time to visit Key Colony Beach?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$75,217 GYDG$86,917 GYDG$86,917 GYDG$65,188 GYDG$58,084 GYDG$60,591 GYDG$63,098 GYDG$58,502 GYDG$49,935 GYDG$50,980 GYDG$58,502 GYDG$73,127 GYD
Avg. temp21°C22°C24°C25°C27°C29°C30°C30°C29°C27°C25°C23°C

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

  • Total vacation rentals

    Explore 390 vacation rentals in Key Colony Beach

  • Nightly prices starting at

    Key Colony Beach vacation rentals start at G$29,251 GYD per night before taxes and fees

  • Verified guest reviews

    Over 15,660 verified reviews to help you choose

  • Family-friendly vacation rentals

    330 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wi-Fi availability

    380 of Key Colony Beach vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Key Colony Beach rentals

  • 4.9 Average rating

    Key Colony Beach stays are highly rated by guests—averaging 4.9 out of 5!

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