Holiday rentals with a kayak in Key Colony Beach

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, 74 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

5 out of 5 average rating, 13 reviews

Water Views | Private Pool Oasis + Gazebo + Kayaks

Modern 4BR/4.5BA waterfront getaway in Marathon’s Coco Plum, set on a wide open canal with gorgeous water views—perfect for boaters, families, and friend groups. Spend your days in the huge private pool, relax under the gazebo, and come home to a newer, beautifully kept 2012 house designed for easy Keys living. 🏊 Huge private pool + gazebo (with poolside bathroom) 🛶 Kayaks included + big open-canal view ⚓ Pier-style dockage for your boat or rental boat 🌅 Wraparound covered porch for sunrise/

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 out of 5 average rating, 30 reviews

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

Cielo's Del Mar 1 is a luxurious new construction duplex home located within walking distance of Key Colony's best waterfront dining restaurants and beaches. This spacious home comes equipped with 40' of dockage, outdoor swimming pool, spacious balconies and plenty of games for enjoyment. The home was designed with vacation and relaxation in mind, it is the perfect place for family and friends to enjoy time together. Big families can rent both sides of the duplex home for larger gatherings!

A modern kitchen features granite countertops and a large island with seating. Natural light floods the space through multiple windows. Light-colored cabinetry contrasts with vibrant blue tile accents, creating a welcoming atmosphere. The kitchen opens to a living area, showcasing comfortable seating and views of the outside.

4.95 out of 5 average rating, 37 reviews

Salt&Seaglass. Key Colony. Screen Porch. Pool Club

This Key Colony Beach home is a welcoming, modern canal-front duplex home provides a relaxing and comfortable atmosphere for your vacation in the Florida Keys! The home features 2 large bedrooms and 2 bathrooms, a modern kitchen with large island and granite counter tops, a master bedroom with private bathroom and modern, plank flooring tile throughout the home. Enjoy the relaxing 9 X 20 ft porch & comfortable furniture. Outside: Lounge chairs & other seating, a kayak, a 37 foot dock

An outdoor seating area features a large rectangular table surrounded by six cushioned chairs. Two bright umbrellas provide shade, while lush palm trees frame the scene. A clear view of the private dock and waterway is visible in the background, complementing the coastal setting.

5 out of 5 average rating, 16 reviews

Cabana Club, Kayaks, Pets, Boat Dock, Near Golf!

Welcome to Latitude Adjustment – Your Slice of Paradise in Key Colony Beach! Escape to Latitude Adjustment, a beautifully appointed 4-bedroom, 2-bathroom retreat located at Key Colony Beach (Sleeps 7). Just steps from pristine beaches and vibrant local attractions, this home offers the perfect blend of comfort, style, and coastal charm. Whether you’re relaxing indoors or soaking up the Florida sunshine outdoors, Latitude Adjustment provides everything you need for an unforgettable getaway.

4.96 out of 5 average rating, 187 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 Villa

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!

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, 76 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

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, 140 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.

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, 29 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, enjoy the outdoor TV after a day on the water, & grill your catch. Relax on the upper deck sunbathe and enjoy the vistas!

4.93 out of 5 average rating, 117 reviews

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.

Apartment in Marathon

Waterfront Condo, daily housekeeping & breakfast!

Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and resort amenities including a pool, Tiki Bar, restaurant, Marina, and more. Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

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.

4.77 out of 5 average rating, 56 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!

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

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, 17 reviews

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

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, 34 reviews

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

5 out of 5 average rating, 13 reviews

Best Location in Marathon & KCB!

A large heated swimming pool is set against a backdrop of lush palm trees and water views. The stone patio surrounding the pool provides ample space for relaxation, while vibrant greenery enhances the tranquil atmosphere.

4.96 out of 5 average rating, 96 reviews

Key Colony Paradise

A hot tub is set under a blue canopy, inviting relaxation. Adjacent, outdoor seating with colorful chairs is positioned near the water, framed by palm trees and an American flag. The calm canal reflects the vibrant surroundings, enhancing the tranquil atmosphere.

4.95 out of 5 average rating, 58 reviews

Experience the Ultimate Florida Keys Getaway.

An aerial view captures the property's prime location along the waterfront, highlighting proximity to Sombrero Beach and the 7 Mile Bridge. The tranquil waters and nearby coastal homes enhance the inviting atmosphere of this tropical getaway.

5 out of 5 average rating, 6 reviews

Waterfront Oasis3/2 Direct Ocean

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.

4.88 out of 5 average rating, 48 reviews

Coral House: Your Perfect Get-Away!

Other holiday rentals with a kayak

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.

4.98 out of 5 average rating, 83 reviews

Sombrero beach vacation paradise, great location

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

4.91 out of 5 average rating, 44 reviews

Dog-Friendly • Pool & Boat Dock • Sombrero Beach

4.92 out of 5 average rating, 84 reviews

A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.

Houseboat in Marathon

b watervibe

4.88 out of 5 average rating, 50 reviews

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

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, 20 reviews

Boating Paradise Villa rental Lic# VACA-25-124

Superhost

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.

4.85 out of 5 average rating, 52 reviews

Viamarhe House-Private beach, Kayak, yard games

An aerial view captures a waterfront property featuring multiple pools surrounded by lush greenery. The colorful houses are highlighted against the clear blue water, with the distant horizon blending into the sky. Nearby homes and a small marina are visible, adding to the serene setting.