Holiday rentals with a kayak in Key Colony Beach

5 out of 5 average rating, 10 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 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!

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.

4.82 out of 5 average rating, 28 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!

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!

An airy open-concept living space features a dining area with a round table and chairs, complemented by a decorative centerpiece. Light-colored walls enhance the brightness from sliding glass doors that offer views of the screened porch and canal outside, while ceiling fans circulate gentle breezes.

4.9 out of 5 average rating, 52 reviews

Tradewinds in Key Colony Beach. XL Porch, Dock

Beautifully appointed 3 Bedroom, Duplex is renovated & has New furniture & high quality mattresses. This welcoming canal front home provides a relaxing and comfortable atmosphere for your vacation in the Florida Keys! Huge screened-in porch, Canal, Dock and full set of amenities! Comes with free use of the CABANA CLUB, a private swim club with a temp controlled pool & Beach. 8 blocks away. The property is surrounded by lush foliage & high fencing so you can enjoy a private setting.

4.96 out of 5 average rating, 183 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 - Kayaks - 2-Bedroom, 2.5-Bathroom 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!

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, 135 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!

Superhost

5 out of 5 average rating, 3 reviews

Kayak, Pet-Friendly, Boat Dock & Cabana Club

Fins to the Left – Key Colony Beach 2 Bedrooms • 2 Bathrooms • Sleeps 5 • Pet Friendly • Access to the Cabana Club Welcome to Fins to the Left, a waterfront retreat in the heart of Key Colony Beach where island living meets comfort and convenience. This beautifully updated, stilted half-duplex offers two king bedrooms, two full bathrooms, and space to sleep up to five guests—perfect for small families or couples looking to unwind in true Keys style.

Superhost

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

4.88 out of 5 average rating, 137 reviews

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

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!

Popular amenities for Key Colony Beach kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House 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

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, 77 reviews

Sombrero beach vacation paradise, great location

The image showcases a modern two-story home with a light blue exterior, surrounded by lush landscaping. A heated pool is visible in the foreground, alongside kayaks and paddle boards. The ocean view offers clear, open water, enhancing the tranquil setting of 'The 7-Mile Villa.'

5 out of 5 average rating, 31 reviews

World-Class Oceanfront Pool/Hottub Sunset Escape

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, 71 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

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, 15 reviews

Boating Paradise Villa rental Lic# VACA-25-124

The outdoor area showcases a private heated pool surrounded by lounge chairs. Lush greenery is present, along with a staircase leading to the upper level of the home. The canal is visible in the background, with boats moored along the dock under a clear blue sky.

4.89 out of 5 average rating, 18 reviews

*NEW!*Paradise Palms~Dock~Pool~Kayaks Grill~View!

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.

4.98 out of 5 average rating, 44 reviews

Waterfront Home| Heated Pool + Dock+Kayaks

Other holiday rentals with a kayak

An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.

5 out of 5 average rating, 40 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

4.91 out of 5 average rating, 33 reviews

Private Dock| 5min beach| Kayak| Sunset view|RV

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, 56 reviews

Experience the Ultimate Florida Keys Getaway.

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, 14 reviews

Apartment in Marathon

New Waterfront Views | Pool & Tiki Bar

4.94 out of 5 average rating, 71 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

An open-concept living area is featured with light wood flooring and large windows allowing natural light. A modern dining table is set for four, while a cozy seating area includes a sofa and decorative wall art. Nautical elements enhance the coastal ambiance.

5 out of 5 average rating, 24 reviews

Marathon Paradise

A spacious pool area is surrounded by patio tiles, featuring two green lounge chairs and multiple seating options for relaxation. Palm trees and a canal are visible in the background, enhancing the outdoor ambiance. The clear blue sky reflects a pleasant atmosphere.