Vacation 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.

4.95 out of 5 average rating, 59 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, 62 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

Captains Quarters, Your 4BR Waterfront Oasis on a deep-water ocean canal. This meticulously remodeled home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 75ft dock with sailing kayaks for ocean adventures 🕹️ Epic game room with Golden Tee, Pack Man, foosball table, Ping Pong & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

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.

4.92 out of 5 average rating, 25 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.

5 out of 5 average rating, 20 reviews

Welcome to Paradise! Private Pool, Kayak, SUPs

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, 28 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.

4.96 out of 5 average rating, 24 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

4.96 out of 5 average rating, 158 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 - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg

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.

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, 129 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 shaded outdoor seating area features white cushioned chairs surrounding a dark wooden table. Brightly colored kayaks are visible on the water's edge, alongside a boat dock. Lush greenery encircles the space, complementing the serene canal views.

4.93 out of 5 average rating, 71 reviews

Waterfront Villa Bring Your Boat Cabana Club Beach

Beautiful, clean 2/2 villa with 40ft dock- bring your boat up to 50ft. Open concept with water views, great location in beautiful Key Colony Beach, walk to the beach, pool and tiki bar at the Cabana Club (membership included with the rental), close to Marathon and centrally located between Islamorada and Key West. Relax and grill on the back patio or use of our ocean kayaks on the beautiful canal. 10 minute ocean and gulf access, close to restaurants, shopping and nightlife.

A comfortable brown leather sofa is adorned with striped decorative cushions and a prominent 'love home' pillow. A wooden coffee table holds various brochures and a remote. In the background, fishing rods are visible, and a neutral-colored wall adds to the relaxed atmosphere.

4.89 out of 5 average rating, 28 reviews

Pet Friendly (Fee-Less) Half-Duplex Cottage

We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with many amenities. The cottage has a large yard and plenty of room to park boats, RVs, and wave runners. This modernized cottage is for you if you all need a great place to stay. This quaint and cozy home offers good value and features new furniture and brand-new state-of-the-art stainless steel appliances. There is one bedroom and a pull-out queen-size sofa bed.

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

4.89 out of 5 average rating, 123 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 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.

4.95 out of 5 average rating, 43 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.

Popular amenities for Key Colony Beach kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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.

5 out of 5 average rating, 22 reviews

Seaside Sunrise. Newly remodeled waterfront

An aerial view captures the canal-front neighborhood, showcasing tree-lined streets and houses with turquoise roofs. The winding canal leads toward the open turquoise waters in the distance, emphasizing the area's coastal charm and accessibility to boating activities.

4.93 out of 5 average rating, 40 reviews

Oasis Canal-Front Home: Pool, Dock, BBQ, and more!

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, 72 reviews

Sombrero beach vacation paradise, great location

4.95 out of 5 average rating, 139 reviews

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

A boat is docked beside a light blue cottage, featuring large windows that reflect on the water's surface. Lush palm trees surround the property, enhancing the tropical atmosphere and offering a serene view of the canal.

4.98 out of 5 average rating, 53 reviews

Flamingo Palms-NOV/DEC discounts on AVAIL DATES

A spacious pool area is framed by tropical landscaping, showcasing a large, clear swimming pool. Sun loungers are arranged around the pool, providing places to relax. A tiki hut offers shaded seating options, enhancing the outdoor living experience with serene water views.

4.8 out of 5 average rating, 40 reviews

Luxury Waterfront Retreat with Dockage & Pool

A private pool is surrounded by a paved patio, featuring lounge chairs and a small table. Lush tropical plants provide a natural backdrop. In the distance, a boat dock is visible along with outdoor dining furniture and an umbrella. Soft lighting enhances the inviting outdoor space.

5 out of 5 average rating, 18 reviews

Waterfront home w/pool, dock & close to beach

The outdoor area is softly illuminated with multicolored lights, outlining the space. A set of colorful stools sits invitingly near a grassy section, while a staircase leads to the entry. The façade of the home is visible, creating a welcoming ambiance at night.

4.97 out of 5 average rating, 34 reviews

COZY Family Home- 5 minutes from sombrero beach

Cottage rentals with a kayak

A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.

4.81 out of 5 average rating, 102 reviews

OCEANIA... water front cottage retreat ~

4.97 out of 5 average rating, 93 reviews

A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.

Cottage in Islamorada

Islamorada bungalow 2 bed & pool

A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.

4.71 out of 5 average rating, 163 reviews

Calypso Cottage

A coastal view features multiple white houses with balconies situated along the waterfront. Palm trees sway gently in the breeze, and clear blue skies create a serene backdrop. Vehicles are parked in the driveways, emphasizing accessibility to the beachfront.

4.94 out of 5 average rating, 18 reviews

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

An open living area features warm wooden beams on the ceiling and large windows allowing ample natural light. A rustic coffee table is centered on a patterned rug, with a comfortable sofa positioned nearby. Barstools line a counter, creating a casual dining space.

Cottage in Islamorada

4.76 out of 5 average rating, 177 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

4.94 out of 5 average rating, 146 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

A guest room features a queen-sized bed adorned with a floral comforter. Two wooden nightstands with lamps flank the bed. French doors open to the outdoor garden, while light-colored curtains soften the sunlight filtering in from the windows.

Private room in Key Largo

4.58 out of 5 average rating, 740 reviews

Cottage Sunroom Waterfront Retreat 2 ppl

Cottage in Key Colony Beach

The private saltwater pool is framed by tropical plants and bright blue sky. Lounge chairs are positioned nearby, alongside decorative elements and pots. The serene atmosphere offers a refreshing retreat, inviting relaxation and enjoyment in the beautiful surroundings.

5 out of 5 average rating, 12 reviews

Luxurious Oasis on: 2BR w/Private Pool, Tiki, Dock

Other vacation 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, 28 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

4.81 out of 5 average rating, 21 reviews

A modern game area features a slate bumper pool table surrounded by turquoise chairs. A wall-mounted dartboard adds to the entertainment options. The adjacent kitchen, equipped with stylish cabinetry and contemporary appliances, is partially visible, providing a seamless flow between activities.

Condo in Marathon

Reel Hip– Heated Pool, Boat Slip, Heat, King Bed

Superhost

An aerial view showcases a vibrant waterfront community with colorful homes lining the canal. A serene blue pool is visible in front of one residence, while boats can be seen docked along the waterfront. The tranquil ocean extends into the horizon, under clear blue skies.

5 out of 5 average rating, 9 reviews

Discount to Jan 31! Direct to Ocean! Fun Amenities

4.95 out of 5 average rating, 22 reviews

A sandy shoreline is bordered by swaying palm trees, providing a peaceful oceanfront view. A yellow kayak rests on the beach, while a hammock is visible nearby, adding to the tranquil setting. The distant jetty extends into the calm sea, enhancing the serene atmosphere.

Guesthouse in Marathon

The Pink Dolphin House.

5 out of 5 average rating, 7 reviews

Townhouse in Marathon

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

A private backyard showcases a tranquil pool surrounded by a stone deck. Comfortable lounge chairs are positioned for relaxation, with a vibrant float placed in the water. The blue exterior of the house enhances the outdoor space under a partly cloudy sky.

4.93 out of 5 average rating, 83 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

4.97 out of 5 average rating, 67 reviews

A welcoming living area features a dark gray sofa and armchair, complemented by patterned cushions. A light wooden coffee table sits atop beige tile flooring. A large flat-screen TV is mounted on the wall, and natural light filters through window coverings, creating a bright atmosphere.

Apartment in Marathon

Dock POOL Kayaks Bikes Beach2mi WalkToStores

An inviting outdoor area features a swimming pool surrounded by a manicured lawn. Comfortable lounge chairs provide ample seating, and a large umbrella offers shade. A canal with docked boats is visible in the background, complemented by palm trees swaying in the breeze.