Vacation rentals with a pool 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, 129 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.

A private inground pool is surrounded by palm trees under a clear blue sky. A colorful rubber duck floats on the water's surface. A hammock can be seen in the background, while a red umbrella provides shade over two seated chairs nearby, creating a serene outdoor setting.

4.86 out of 5 average rating, 36 reviews

Welcome to Paradise! Private Pool, SUPs, Kayak!

Paradise Awaits You!! With a Beautiful Private Pool, 40’ Dock, Kayaks, SUPs, & Bikes; Welcome to Paradise is the Perfect Place to Stay & Play in the Sun & on the Water! Our home w Breezy Palms is centrally located w Beaches, Boating, Fishing, Diving, Swimming, Dining & Refreshing Cocktails just minutes away! We are owners, Luis & Aysie. We put all our love of the Keys into our home, & we just know you will love it too. Message us or book instantly & start planning your trip to Paradise!

4.97 out of 5 average rating, 286 reviews

Amazing Ocean Front Views Key Colony Beach

Everything is brand new in this gorgeous condo with amazing oceanfront views. #40 has two queen beds, well equipped kitchen with full-size appliances and everything you need to cook & serve meals. Fast, reliable WiFi, large SmartTV. Super cold new A/C unit Enjoy stunning views of sunrise from your private balcony & sunsets next door at Sunset Park. Heated pool, beach BBQs & tiki huts for guest use We are centrally located to awesome Keys adventures just a few miles drive from the condo.

5.0 out of 5 average rating, 6 reviews

Entire private two family water front home.

Forget your worries in this spacious and serene space. This is a great option for large multi-generational families that want to be in two separate areas of a full home. This is a full two family home with separate entrances. Enjoy 75 feet of waterfront with a concrete seawall, davits, a fish cleaning station, and direct ocean and bay access via nearby Vaca Cut. The home offers full privacy, a private heated and chilled pool in the heart of Key Colony Beach; the entire home is yours!

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.

4.95 out of 5 average rating, 146 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.

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

Beachside Unit 22 - Private Beach on Atlantic

Unit 22 Details: Main Floor, Walk-in Shower, 2 Queen Beds and Queen Sofa Pull-out, Maximum Occupancy 4 Guests (0-2 years old count as a guest), 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.”

4.86 out of 5 average rating, 153 reviews

5.0 out of 5 average rating, 6 reviews

Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

4.89 out of 5 average rating, 9 reviews

P06 - Charming 2 bed, 2 bath half duplex with dock

Charming and cozy 2 Bedroom, 2 bathroom all ground level, half duplex offering deep-water dockage. Located in fabulous Key Colony Beach. This home comes with access to Key Colony Cabana Club. Key Colony Beach is a small, friendly, walkable island in the heart of Marathon, the Florida Keys. Located mere minutes from beaches, bike and running paths, golf courses, tennis courts, the Dolphin Research Center, Aquarium Encounters and the Turtle Hospital. - Maximum Occupancy: 4

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, 132 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 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.

4.95 out of 5 average rating, 148 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.

5.0 out of 5 average rating, 23 reviews

*New* Turtles Pace-Private Beach

Discover the perfect getaway in this beachfront condo in Key Colony Beach, FL. With direct access to a private beach, you’ll enjoy breathtaking ocean views and endless relaxation. This condo features modern amenities, a fully equipped kitchen, and comfortable living spaces. Whether you’re soaking up the sun on the beach or exploring local attractions, this is the ultimate coastal escape. Don't miss the chance to experience paradise!

A shaded outdoor area features a small private pool surrounded by lounge chairs. A white table sits nearby, offering a space for refreshments. A view of the boat dock and palm trees creates a relaxing atmosphere perfect for enjoying sunny days.

4.96 out of 5 average rating, 47 reviews

Villa Bella 3/3 with Private Pool & NEW Dock!

Relax with the whole family at this newly remodeled waterfront property with private pool , 38 foot private dock, bait freezer, and plenty of parking for your boat trailer on-site. The home is pet friendly. Cabana Club access is included. The home is managed by Florida Keys Vacation Rentals. 2-person Malibu XL Ocean Kayak to use during your stay!

Popular amenities for Key Colony Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view captures the Snapper House situated alongside expansive canals, with direct access to the water. A red marker highlights the property’s location. Surrounding homes and palm trees create a vibrant neighborhood environment, reflecting the essence of coastal living.

4.92 out of 5 average rating, 160 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

A hot tub is situated on a stone patio, surrounded by lush tropical greenery and swaying palm trees. The sparkling water invites relaxation, while a staircase leads from the patio to the serene canal and dock area in the background.

4.86 out of 5 average rating, 43 reviews

Kayaks, Cabana Club, Hot Tub, Deep Water Dock

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.

4.88 out of 5 average rating, 17 reviews

Key Colony Beach Waterfront 321

4.94 out of 5 average rating, 78 reviews

Waterfront Villa Bring Your Boat Cabana Club Beach

A spacious Tiki Hut featuring comfortable seating arrangements, with two plush armchairs and a central coffee table. The ceiling fan hangs overhead, and the area is adorned with whimsical decorations, including fish motifs, while offering views of the canal and surrounding boats.

4.92 out of 5 average rating, 37 reviews

TropiCarribean - Pool Club, Canal, XL Tiki Hut!

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.

5.0 out of 5 average rating, 98 reviews

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

A light-filled living area features a comfortable seating arrangement with leather sofas and a large area rug. A television is housed within a white entertainment unit, flanked by decorative glass vases. Expansive sliding glass doors open to the outside, providing an airy ambiance.

4.95 out of 5 average rating, 81 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

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.

4.97 out of 5 average rating, 86 reviews

KCB Tiki Hut Oasis: 37.5' Dock + Cabana Club!

Condo rentals with a pool

A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.

4.97 out of 5 average rating, 120 reviews

Slip, Private Ramp, Pool, Trailer Parking, Freezer

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.

4.92 out of 5 average rating, 120 reviews

Dapper Dolphin | Canal View + Breakfast + Pool

Lounge chairs are positioned on the grass near the ocean, surrounded by palm trees. A soft gradient of colors in the sky, transitioning from pale pink to light blue, is visible above the tranquil waters. Rocky shoreline meets the beach, creating a peaceful environment.

4.96 out of 5 average rating, 52 reviews

Paradise found! Sea-Esta Condo beach and pool.

An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.

5.0 out of 5 average rating, 29 reviews

Private Beach in Marathons Key Colony Beach

4.93 out of 5 average rating, 42 reviews

*NEW* Private Beach, pool & fully loaded kitchen

4.81 out of 5 average rating, 16 reviews

Anglers Paradise ~ Waterfront Condo with Boat Slip

A serene bedroom is presented with a spacious bed dressed in blue and white linens. Tropical-themed artwork is displayed above the bed, complemented by two bedside lamps. Natural light filters through sheer curtains, and wood flooring adds warmth to the inviting space.

4.84 out of 5 average rating, 38 reviews

Peaceful, Newly Renovated Condo With Boat-slip.

A balcony view overlooking the Gulf of Mexico features a railing framing the scenic water below, where sunlight glimmers on the surface. Lush greenery is visible nearby, enhancing the serene coastal atmosphere.

4.95 out of 5 average rating, 56 reviews

2-story condo w/ panoramic bay views and balconies

Other vacation rentals with a pool

Apartment in Key Colony Beach

The room features two spacious beds with light-colored bedding, complemented by decorative pillows. A ceiling fan is present above, while large windows with shutters allow natural light. Colorful artwork depicting flamingos adorns the walls beside bedside tables and lamps.

2 Bdrm Oceanfront Complex Private Beach & Pool

4.93 out of 5 average rating, 41 reviews

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.

Castillo Del Mar- Ocean access from your backyard

5.0 out of 5 average rating, 15 reviews

Townhouse in Key Colony Beach

A private pool glistens under the bright sky, accompanied by lounge chairs and tropical landscaping. The canal is visible in the background, with a paddle board propped against the wall, enhancing the modern coastal ambiance of the outdoor space.

Cabana Club Privileges! Paddleboards, Bikes, Kayak

5.0 out of 5 average rating, 7 reviews

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.

5.0 out of 5 average rating, 19 reviews

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

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.

4.91 out of 5 average rating, 33 reviews

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

A modern duplex home features a spacious outdoor area with a swimming pool surrounded by lounge chairs. The structure is two stories with multiple balconies overlooking the pool, while tropical greenery provides privacy along the perimeter.

5.0 out of 5 average rating, 30 reviews

Cielo's Del Mar 1 - Pool/Dock/Beach Luxury in KCB

4.86 out of 5 average rating, 7 reviews

Home in Marathon

DOCK-Beach Club-Tiki Hut-Screened Porch-East Yard