Holiday rentals with a kayak in Key Colony Beach

5 out of 5 average rating, 11 reviews

Best Location in Marathon & KCB!

Luxury Meets Adventure at Seahorse Landing! 40’ of dockage, SUP, kayak & all the equipment you’ll need to explore the beautiful bays & wildlife frequented waterways. All that adventure is balanced by a newly renovated interior offering the perfect blend of comfort and style in a modern, spotless setting. Our family has created a home that is a perfect fit for adventurous couples or families seeking relaxation& exploration. Send us a message or book instantly & begin your luxurious adventure!

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.

4.96 out of 5 average rating, 69 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

Key Colony Beach is truly the gem of the Keys! Located in the middle keys near Marathon, we are a convenient drive to nearly all activities in the Keys. Visit Key West for the day, take a fishing charter in Marathon, or snorkel/scuba at John Pennekamp Park in Key Largo. We love Key Colony Beach for it's small town feel, easy pedestrian paths all over the island for biking, running, and walking, and great restaurants. We provide Cabana Club Membership for easy beach and pool access with a tiki

A private pool is bordered by lush palm trees and a thatched Tiki Hut. Lounge chairs are arranged around the pool area, and colorful outdoor decor adds a cheerful touch. Clear blue skies and sunshine illuminate the space, creating an inviting outdoor retreat.

4.93 out of 5 average rating, 27 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

Beautiful Key Colony Beach waterfront duplex with a private pool! Featuring a newly updated, 3/2, spacious 1440 sf home, deep water private boat slip & lift, Tiki Hut w/TV, kayaks, pet friendly, ice machine, bait freezer, large kitchen, Cabana Club, restaurant, and beach access. Family friendly location w/Golf, a playground, and dog park. Sit under the tiki hut, watch the game on the outdoor TV after a day on the water, & grill your catch. Relax on the upper deck sunbathe and enjoy the vistas!

4.96 out of 5 average rating, 184 reviews

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

Beach House Getaway - Free Kayaks 2/2.5

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

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.

5 out of 5 average rating, 5 reviews

Cabana Club Privileges! Paddleboards, Bikes, Kayak

Located in Key Colony Beach, The Blue Manatee (formerly Sunshade Villa) on KCB is a gorgeous, canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool and all the amenities you would want for an amazing vacation in the fabulous Florida Keys! The Blue Manatee has CABANA CLUB PRIVILEGES! The Cabana Club in located in Key Colony Beach on the ocean. It has a large pool, beach area, tiki bar and restaurant with a full menu!

Superhost

A tropical backyard features a private saltwater pool surrounded by seating areas. A thatched-roof Tiki Hut is adorned with string lights. A gas fire pit sits centrally, while walls are embellished with colorful fish murals. Lush greenery completes this inviting outdoor space.

4.91 out of 5 average rating, 109 reviews

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill!

Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

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.

Superhost

A serene canal view is showcased, with palm trees framing the scene. The calm water reflects the surrounding greenery and residential structures, creating a relaxing atmosphere. A landscaped area with small stones and plants leads to a white dock, providing direct access to the water.

4.8 out of 5 average rating, 55 reviews

Key Colony Beach House with Cabana Club membership

This is a spacious, open layout, ground level home that can accommodate up to 6 guests with plenty of room to spare (One of the largest 2/2's in Key Colony Beach with 5 beds). It is a short walk from multiple restaurants, bars, waterfront parks, and the Cabana Club. We are located on the ocean side with immediate access to the gulf through Vaca cut. Whether you are planning a fishing vacation, family getaway or both, this home will not disappoint and is the ultimate getaway!

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

Professionally decorated, spacious, canal view keys home located in Key Colony Beach, the “Gem” of the Florida Keys. Featuring 2BR 2BA accommodating up to 6 ppl in a large & open living room & backyard, provided w/2 bikes, 2kayaks, grill, and 2 minutes walk to Sunset park, it is the perfect Florida Keys getaway for your family. This location is in the heart of the Florida Keys only 45 minutes from Key West and 35 minutes to Islamorada.

A scenic view of a wide canal is presented, lined with palm trees and residential properties. Boating vessels are seen docked along the sides, with clear blue skies and scattered clouds above, reflecting the relaxed atmosphere of the area.

4.94 out of 5 average rating, 33 reviews

3/2 Waterfront/Private dock/Beach & Pool Access

Location, location, location! The Starfish House is walking distance from everything and perfectly centered in the fishing capital of the world! Steps from a golf course, basketball, tennis, bocce ball courts, playground & more. Enjoy live music and drinks at the famous Havana Jack’s just down the street. Centrally located in the Middle Keys—only 1 hr to Key West and 30 min to Islamorada—there’s something fun for every age!

The exterior features a two-story turquoise house with large windows. A private saltwater pool is surrounded by lounge chairs, offering a relaxing space. Kayaks are visible in the background, with palm trees framing the scene under a colorful sky.

4.97 out of 5 average rating, 36 reviews

Ocean's Edge Retreat

Ocean's Edge Retreat is a 3 bedroom / 3 bath home with open water views of the Atlantic Ocean. It includes Cabana Club access, a private new saltwater pool and spa, kayaks and a 40 ft dock for boats. Stunning views of the canal and ocean from the private upstairs master balcony. Kids playground across the street make this an ideal vacation for families. Come see what Ocean's Edge Retreat has to offer!

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.

4.84 out of 5 average rating, 38 reviews

Kayaks, Cabana Club, Hot Tub, Deep Water Dock

Reel Catch UPDATED CANAL FRONT, CABANA CLUB 2/2, with DOCK ** CABANA CLUB ACCESS - Includes private beach, swimming pool, whirlpool & tiki bar with food & drinks! Cast a line and kick back while you enjoy a beautiful Key Colony Beach sunrise from this freshly remodeled 2/2 canal front half-duplex. Boasting 37.5’ of deep water dockage and a 100' wide canal, this home is every fisherman’s dream.

Popular amenities for kayak rentals in Key Colony Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A spacious pool area features a crystal-clear swimming pool surrounded by lounge chairs. A thatched roof gazebo provides shaded seating. Lush greenery and tranquil waters are visible in the background, creating a serene outdoor environment.

4.89 out of 5 average rating, 57 reviews

Stunning Waterfront Retreat with Dockage & Pool -C

An outdoor seating area features a thatched roof, providing shade over a collection of cushioned seating and a low coffee table. A swimming pool is visible in the background, surrounded by tropical greenery. Large glass doors lead into the interior of the home.

5 out of 5 average rating, 49 reviews

Tiki Hut w/TV, Pool, Kayak, Paddleboards, Bikes!

Superhost

A view of the waterfront features a wooden dock lined with white posts. Comfortable seating is positioned alongside vibrant greenery and colorful flowers, offering a serene environment with clear water in the background and a distant shoreline visible.

4.88 out of 5 average rating, 8 reviews

Oceanfront Pool Home - 130ft Dock & Canal Garden

4.93 out of 5 average rating, 42 reviews

Canal Dock • Heated Pool • Walk to Sombrero Beach

A two-story home is showcased, featuring a spacious backyard with a swimming pool surrounded by lounge chairs and umbrellas. The exterior is illuminated under a twilight sky, while a stone walkway leads to the inviting entrance. Lush greenery adds a vibrant touch to the setting.

5 out of 5 average rating, 53 reviews

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

4.93 out of 5 average rating, 72 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

A waterfront property is depicted, featuring a contemporary two-story design with light blue and yellow exterior accents. A private dock is visible alongside the house, and a clear sky reflects over the calm water, enhancing the serene coastal environment.

5 out of 5 average rating, 17 reviews

Boating Paradise Villa rental Lic# VACA-25-124

A sandy beachfront is framed by palm trees, with the glistening Atlantic ocean in the background. A volleyball net is set up on the sand, along with multiple seating areas for relaxation, inviting guests to enjoy the tranquil environment and scenic views.

4.92 out of 5 average rating, 49 reviews

Viamarhe House-Private beach, Kayak, yard games

Other holiday rentals with a kayak

A modern beach house is presented with a light-colored exterior, surrounded by a pebbled landscape. Palm trees are visible, providing a tropical feel. The building features large windows and a distinct entryway, enhancing its architectural appeal.

4.96 out of 5 average rating, 25 reviews

Seaside Sunrise. Newly remodeled waterfront

A serene waterfront view features a private dock extending over calm green waters. Lush palm trees sway gently in the breeze, while a tiki hut with a thatched roof is visible in the background, hinting at a relaxing outdoor space.

5 out of 5 average rating, 36 reviews

Amazing New Waterfront Home, Dock, Pool/Beach Club

Aerial view of a waterfront home surrounded by the Atlantic Ocean and patch reefs. Lush palm trees dot the landscape. The canal is seen flowing between two rows of homes, with boats docked along the private docks, showcasing easy access to the water.

4.93 out of 5 average rating, 86 reviews

Oceanside, Fee-Less Pet, with kayaks - 60 FT Dock

A two-story house is surrounded by lush greenery and palm trees. A spacious backyard features a heated pool and a wooden dock. Loungers are arranged near the pool, providing a relaxing outdoor space. The exterior showcases large windows and a balcony with seating.

4.97 out of 5 average rating, 79 reviews

Sombrero beach vacation paradise, great location

An aerial view of a two-story house situated by a deep-water canal. The property features a private pool and a dock for a boat. Lush palm trees surround the outdoor area, with a spacious patio that includes seating and dining spaces.

4.93 out of 5 average rating, 14 reviews

Steps away from Cabana Club One house, two options

5 out of 5 average rating, 19 reviews

An aerial view captures a unique domed waterfront home surrounded by lush greenery and nearby canals. The property features a spacious outdoor area, with boats docked along the calm waters. A scenic glimpse of the expansive Gulf can be seen in the background.

Dome in Marathon

Your vacation Dome is here!

5 out of 5 average rating, 19 reviews

Flat in Marathon

New Waterfront Views | Pool & Tiki Bar

An outdoor tiki hut provides a shaded seating area with comfortable wicker furniture. Decorative cushions adorn the sofas, and a hammock hangs nearby. Lush greenery surrounds the space, offering a relaxing spot for gathering or unwinding.