Family-friendly holiday rentals in Key Colony Beach

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.

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.

Condo in Key Colony Beach

4.93 out of 5 average rating, 258 reviews

Exquisite Luxury Oceanfront Complex Key Colony

Beautifully renovated condo with all new kitchen & bathroom. #3 has 2 queen beds, fully equipped kitchen with full-size appliances & everything you need to cook and serve meals. Walk-in shower, free and reliable WiFi and SmartTV for watching your favorites. 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.

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

4.93 out of 5 average rating, 136 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Townhouse in Key Colony Beach

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.

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

Guest suite in Key Colony Beach

A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.

4.99 out of 5 average rating, 135 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

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 !

4.8 out of 5 average rating, 5 reviews

P13 - Loggerhead House 3 Bedroom Home with Private

The Loggerhead House A beautiful home in a premier location! This stunning 3-bedroom, 2-bathroom canal-front retreat offers the perfect combination of comfort, style, and island living. Featuring a spacious single-level layout with an open floor plan and easy accessibility, guests can relax and spread out while enjoying all the comforts of this tropical getaway. Step outside to your private backyard oasis complete with a charming tiki hut, perfect for evening cocktails, outdoor ...

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.

4.94 out of 5 average rating, 138 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.

5 out of 5 average rating, 53 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!!

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.

4.89 out of 5 average rating, 126 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

The waterfront patio features a wooden dock leading into the calm water, surrounded by neatly arranged lounge chairs and palm trees. The single-story home is seen in the background with large glass doors and windows, allowing for ample natural light.

5 out of 5 average rating, 38 reviews

Boat Dock+King Bed & Cabana Club

2 Bedroom 2 Bath Master with King Bed and Private Bathroom Central Air Conditioning Waterfront Dock with Private Boat Slip on the 7th Street Canal Cabana Club Tiki Bar with Beach Hot Tub and Junior Olympic Pool Patio with Propane Grill Patio Furniture and Sun Lounges Fully Equipped Kitchen and Coffee Bar World Class Sport Fishing Coral Reef Diving and Snorkeling Water Sports Kayaking and Sandbars Crane Point Hammock and Nature Center

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.

4.94 out of 5 average rating, 135 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.

Popular amenities for Key Colony Beach family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious outdoor area features a large wooden swim spa, framed by vibrant greenery and decorative accents. A sun umbrella provides shade over one side, while light-colored tiles and wooden decking surround the spa, creating a relaxing ambiance. The sky is clear with soft clouds.

5 out of 5 average rating, 15 reviews

3Bed 2Bath~Kayaks~Cabana Club~Swim Spa~Fish Equip

5 out of 5 average rating, 16 reviews

Oceanfront Rooftop Views w/ 75ft of Dockage

A renovated house is set on a corner lot, surrounded by palm trees and coral stone landscaping. The exterior features light yellow walls and white accents. A gravel driveway offers ample parking space, complementing the tranquil tropical environment.

4.93 out of 5 average rating, 158 reviews

Marathon Star - home with hot tub

4.95 out of 5 average rating, 103 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 73 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

A private backyard features a hot tub and a shallow pool, surrounded by tropical greenery. Lounge chairs in teal are positioned nearby, and a grill is placed on the concrete patio. The canal is visible in the background, lined with palm trees.

4.94 out of 5 average rating, 53 reviews

Waterfront w/pool and hot tub

4.92 out of 5 average rating, 53 reviews

A spacious living area features a gray sectional sofa adorned with blue accent pillows. Light wood tables complement the hardwood floor. A large painting of a coastal scene is displayed on the wall, and natural light filters in through shuttered windows.

Holiday home in Marathon

Cabana Club Condo: Key Colony Beach, FL

4.84 out of 5 average rating, 134 reviews

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

Villa in Marathon

Villa in Paradise. Plunge pool. Middle of the Keys

Family- and pet-friendly home rentals

The exterior of a charming waterfront home is depicted, showcasing a canal with clear turquoise water. Lush palm trees frame the property, and well-maintained landscaping adds to the serene environment. The two-story building features a spacious porch and multiple balconies, enhancing outdoor living.

4.96 out of 5 average rating, 76 reviews

Coral Lagoon #23- Private Villa Home

A serene canal view is framed by swaying palm trees under a bright blue sky with scattered clouds. A wooden dock extends into the water, surrounded by lush greenery and waterfront properties, reflecting a tranquil atmosphere ideal for relaxation and exploration.

4.67 out of 5 average rating, 6 reviews

Casita Blanca~ Waterfront, Dock, Cabana Club!

An outdoor lounge area features comfortable seating arranged around a dark table. An umbrella provides shade, with vibrant palm trees framing the relaxing space. The waterway is visible in the background, enhancing the tranquil atmosphere.

5 out of 5 average rating, 16 reviews

Waterfront 3BR · 85′ Dock (2 Boats) · Cabana Club

A view from beneath a thatched roof, showcasing calm waters and a gentle shoreline. Palm trees sway in the breeze, with a wooden dock extending towards the ocean. The sky features soft clouds during sunset, creating a peaceful atmosphere.

4.88 out of 5 average rating, 74 reviews

Oceanfront mermaid house pool and dock

A scenic waterfront patio features two comfortable lounge chairs in vibrant teal, positioned on a patterned rug. A soft, colorful sunset is visible in the sky, casting gentle hues over the tranquil water and surrounding mangroves.

4.87 out of 5 average rating, 47 reviews

Coral House: Your Perfect Get-Away!

A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.

5 out of 5 average rating, 124 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

4.9 out of 5 average rating, 39 reviews

Golf Coast Oasis near Sombrero Beach

A bright living area features light-colored furniture arranged for comfort. A spacious sofa is paired with woven accent chairs, offering views through large glass windows overlooking a canal. Light curtains frame the windows, allowing natural light to enhance the room's open feel.

4.92 out of 5 average rating, 12 reviews

Key Colony Beach Waterfront 321

Family-friendly home rentals with a pool

A spacious Tiki Hut offers shade with palm fronds overhead, surrounded by a paved area. A light blue table with matching chairs is arranged under the hut, providing an inviting spot for relaxation beside the canal.

4.96 out of 5 average rating, 80 reviews

Updated Key Colony Tiki Hut-37.5 Dock-Cabana Club

A welcoming exterior view of the property showcases a landscaped front yard with lush palm trees and tropical plants. A brick driveway leads to the entrance, complemented by a wooden privacy fence in the background under a clear blue sky.

4.83 out of 5 average rating, 35 reviews

4/2.5 Waterfront home on Key Colony, Pool, Dockage

A vibrant view of the property showcases a private patio bordered by palm trees, with outdoor seating and a sun umbrella. The canal is visible, alongside the private dock equipped with seating. Bright colors of the home contrast with the clear blue sky.

4.83 out of 5 average rating, 6 reviews

2 Bedroom 2 Bath Retreat with Cabana in KCB

4.82 out of 5 average rating, 11 reviews

A serene outdoor space includes a private pool surrounded by a spacious deck. Palm trees frame the scene, casting shadows on the white tiles. A furnished sitting area can be seen nearby, offering a relaxing spot to enjoy the warm weather.

Home in Key Largo

Newely Renovated 3/2-private pool/dock/cabana club

5 out of 5 average rating, 3 reviews

Lagoona-Matata

A well-manicured exterior showcases a welcoming entrance framed by palm trees and tropical landscaping. A path of laid bricks leads to the front door, while a central fountain adds a tranquil focal point in the soft morning light.

4.6 out of 5 average rating, 47 reviews

Waterfront Oasis with Boat Dock & Pool!

5 out of 5 average rating, 4 reviews

Splash Into Me! 3 BR Key Colony with private pool

The exterior of the newly renovated home is showcased, featuring a large covered porch supported by white columns. Palm trees line the surroundings, and warm lighting illuminates the entrance, creating an inviting atmosphere against the twilight sky.