Waterfront holiday rentals in Key Colony Beach

4.99 out of 5 average rating, 152 reviews

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

Home in Marathon

Sea Ray Cove w/ Pool, Beach, 80' Dock & Tiki hut

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

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.

4.97 out of 5 average rating, 116 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.

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, 143 reviews

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

The Snapper House is a spacious 3/2.5 bed/bath duplex with 45' of canal dock frontage, also Includes the Cabana Club with large pool (food/drinks for purchase) and ocean facing beach. Awning extends to dock from sliding doors. TV package includes 100+ channels Each bedroom and living room has a full size flat screen TV. For best WIFI reception, an extender is available and should be used when in the back bedrooms, it's name is the same as the main house with an "ext" at the end (same pw).

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

4.93 out of 5 average rating, 119 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Guest suite in Key Colony Beach

A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.

4.99 out of 5 average rating, 118 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

A vibrant exterior of a Caribbean-inspired home is presented, featuring light turquoise walls and charming pink shutters. Lush green landscaping frames the gravel driveway, while tropical plants enhance the welcoming appeal. The entryway opens to a sunlit path leading into the property.

5 out of 5 average rating, 38 reviews

Trip Around the Sun 2/2 + dockage & cabana club

Come take a Trip Around The Sun in our Caribbean-inspired, fully renovated Key Colony Beach 2b/2b home on 4th Street with access to the Cabana Club. Amenities include: Mesh WiFi 6 w/ gig-speed internet, 4k LCD TVs w/ Fire Sticks and YouTubeTV subscriptions in living room (58 inch), kitchen (43 inch), master (65 inch) & guest (55 inch) bedroom, full sized washer & dryer, utility sink, 5 burner gas grill, 30 feet of dockage for your boat, fish cleaning station and bait fridge. STR24-000134

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, 128 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 spacious balcony provides views of the ocean and pool area, with comfortable seating arrangements including two chairs and a table. The gentle wave pattern of the sea is visible in the background, along with a poolside and a nearby pier.

4.97 out of 5 average rating, 31 reviews

Ocean Oasis!OceanView-Private Beach/Pool/TikiHuts

Welcome to Ocean Oasis, your tropical haven in Marathon, Florida! Our stunning 2-bedroom, 2-bathroom condo is located at 501 E Ocean Dr, Marathon, FL 33050. Ocean Oasis offers the ultimate beachfront retreat, with a King-sized bed in the master bedroom and two full-sized beds in the second bedroom, comfortably sleeping six. The spacious balcony boasts breathtaking views of the ocean and pool, perfect for sipping morning coffee or enjoying a sunset cocktail. No Pets Allowed.

Apartment in Key Colony Beach

A spacious sleeping area includes a king-sized bed with crisp white bedding and decorative pillows. Metal fish sculptures adorn the wall, complemented by two bedside lamps. A dark sectional sofa is positioned nearby, creating a comfortable seating area for relaxation.

4.92 out of 5 average rating, 302 reviews

Key Colony Beach Luxury Condo, New Modern Interior

Luxury private studio condo, ocean front complex, full kitchen, heated pool, private beach in Key Colony Beach, Florida. Enjoy all new furnishings, newly renovated bathroom and a full kitchen stocked with everything you need to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Beautiful ocean front beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use. We provide Amazon Echo for great music during your stay.

Apartment in Key Colony Beach

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.87 out of 5 average rating, 139 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and 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.”

4.97 out of 5 average rating, 126 reviews

A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.

Home in Marathon

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

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.

4.94 out of 5 average rating, 126 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.

Popular amenities for waterfront rentals in Key Colony Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Superhost

An aerial view of the beachfront condo building is captured, revealing its three stories and proximity to the ocean. Surrounding palm trees enhance the tropical ambiance, while the serene blue water reflects sunlight. A small parking area is visible in front of the property.

4.83 out of 5 average rating, 18 reviews

Seaside Villa~ Charming Beachfront Condo w/ Pool!

An aerial view captures the layout of the Ocean Isles Fishing Village, showcasing multiple light blue condos with white roofs positioned along winding roads. The Atlantic Ocean glimmers in the background, surrounded by lush greenery and residential areas, illustrating the tranquil setting of the Florida Keys.

5 out of 5 average rating, 15 reviews

Oceanfront Getaway in Marathon!

Superhost

Villa 4204 on Duck Key - Boat Slip available

A scenic outdoor area features a thatched-roof gazebo overlooking the ocean. Palm trees sway gently in the breeze, and a paved pathway leads to the waterfront. The blue waters reflect the sky, creating a tranquil coastal atmosphere.

5 out of 5 average rating, 21 reviews

#1 Island Hideaway 89 - OCEAN FRONT

The open living space features a cozy couch and vibrant armchair, with a seating area seamlessly connected to the kitchen and dining space. Large glass doors offer a view of the balcony and serene harbor, allowing natural light to brighten the room.

5 out of 5 average rating, 6 reviews

Boot Key Harbor Penthouse

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.

4.97 out of 5 average rating, 67 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

5 out of 5 average rating, 14 reviews

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.

Flat in Key Colony Beach

2 Bdrm Oceanfront Complex Private Beach & Pool

The resort's outdoor pool area features a clear blue pool surrounded by lounge chairs. Palm trees are seen in the background, alongside a two-story building. Red umbrellas provide shade for guests enjoying the poolside atmosphere under a bright blue sky.

4.61 out of 5 average rating, 929 reviews

Standard 1 Bedroom King Suite with Balcony

Waterfront house rentals

A half-duplex property is featured with light blue exterior walls and white railings. A walkway leads to the upper level accessed by a staircase. Lush greenery lines the side, and two red lounge chairs are positioned on a gravel surface under the shade of palm trees.

5 out of 5 average rating, 80 reviews

Dock, Beach Club, Ocean & Gulf Access, Pickle Ball

An aerial view shows the property in proximity to the Atlantic Ocean, surrounded by palm trees. A dock extends into the clear water, with the colorful buildings of the surrounding area visible. The scene captures a serene coastal landscape, enhancing the appeal of a beachfront getaway.

4.89 out of 5 average rating, 9 reviews

Keys to Ohana. Ocean views. Private Pool, Hot Tub

An aerial view captures the beach house surrounded by lush greenery and neighboring properties along the waterway. A spacious dock extends into the canal, providing easy access to the ocean, while the large rooflines emphasize the coastal architecture.

5 out of 5 average rating, 30 reviews

Easy Ocean Access 30' Dock House Pool Cabana Club

The view showcases a private pool surrounded by a textured patio and sleek railing, overlooking a tranquil canal. Lush greenery lines the waterway, and boats can be seen docked across the canal, contributing to a serene outdoor space.

5 out of 5 average rating, 24 reviews

Modern Island Luxury | 4 En-Suite Masters, 6 BA, P

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

4.95 out of 5 average rating, 42 reviews

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.

Home in Marathon

Waterfront w/pool and hot tub

A two-story house with a yellow exterior is surrounded by palm trees. A red roof and a balcony are visible above the entrance. A paved driveway leads up to the entrance, with a small garden of tropical plants and gravel accents at the base.

4.88 out of 5 average rating, 17 reviews

Fun in the Sun!

A wooden dock extends into a calm canal, surrounded by clear water. Post lights are visible along the dock, and palm trees line the opposite bank. The sky above is partly cloudy, enhancing the tranquil setting.

4.8 out of 5 average rating, 15 reviews

Seas the Day

Waterfront apartment rentals

5 out of 5 average rating, 16 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

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.

4.81 out of 5 average rating, 21 reviews

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

An aerial view showcases the condo surrounded by lush greenery and palm trees, with the vibrant blue waters of the Atlantic Ocean in the background. The surrounding area features a coastal road and distant properties, highlighting a serene atmosphere.

4.9 out of 5 average rating, 29 reviews

Paradise @ MM61 - Waterfront 1 BR / 1 Bath Condo

The image presents a serene waterfront view featuring a calm blue ocean with a wooden dock extending into the water. Several boats are docked along the pier, while palm trees are positioned in the foreground, adding a tropical touch to the landscape.

5 out of 5 average rating, 9 reviews

1BR Snowbird-friendly condo w/heated pool, BBQ, AC

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.

4.94 out of 5 average rating, 47 reviews

2-story condo w/ panoramic bay views and balconies

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.

4.96 out of 5 average rating, 110 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Apartment in Key Colony Beach

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, 47 reviews

Paradise found! Sea-Esta Condo beach and pool.

An aerial view showcases the beachfront location of the condominiums, with a gleaming pool surrounded by well-kept lawns. White sandy beaches meet the clear turquoise waters, while tropical palm trees sway gently in the breeze. Nearby canals and homes create a serene coastal community.