Vacation rentals with a pool in Key Colony Beach

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Top-rated rentals with a pool in Key Colony Beach

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Top guest favorite

An outdoor space features a sparkling in-ground pool surrounded by a sun deck with several lounge chairs. A shaded screened-in porch is visible in the background, along with a gas grill and a cornhole game set nearby. Lush palm trees provide a tropical atmosphere.

Home in Marathon

4.99 out of 5 average rating, 132 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

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.

Guest favorite

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

4.95 out of 5 average rating, 136 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Superhost

An aerial view of a vibrant waterfront neighborhood showcases a pale yellow house surrounded by lush greenery. Nearby, several homes with varying colors and styles line the streets, while a deep canal runs at the back, providing easy waterway access.

Home in Key Colony Beach

4.82 out of 5 average rating, 11 reviews

Key Colony Beach-POOL & DOCK

Escape to a 4-bed, 1800 sq. ft. waterfront haven! On a deep canal opening to Vaca cut this gem offers all you need. The master suite boasts a king bed, there are three queen beds in separate rooms. Dive into the pool or to the private dock for waterway access. Upstairs, an open kitchen with a six-person breakfast bar beckons culinary adventures. Downstairs, an outdoor kitchen invites alfresco delights. This non-smoking sanctuary is more than a rental—it's a canvas for unforgettable moments.

Top guest favorite

An aerial view captures the coastal complex featuring turquoise roofs and landscaped grounds. The private beach is visible, lined with palm trees, lounge chairs, and tiki huts. The calm waters reflect the blue sky, while boats can be seen in the distance.

Condo in Key Colony Beach

4.93 out of 5 average rating, 215 reviews

Anchors Away Condo - Key Colony Beach Oceanfront

Beautiful new renovation in Key Colony Beach ocean front complex. Unit #4 is a studio condo on the 1st floor (no stairs to climb) within steps of the heated pool and private beach. #4 features a crisp, clean white interior with new kitchen, bathroom and furnishings. Kitchen has everything needed to cook a complete meal (dishes, cookware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Guest favorite

A newly built house features a private outdoor pool surrounded by landscaped greenery and stylish seating areas. The spacious yard includes a paving stone design, and a large deck is accessible from the upper floor, highlighted by the Florida sky's vibrant blue hues.

Villa in Marathon

5 out of 5 average rating, 7 reviews

Villa Marlin - Perfect Vacation in Florida Keys

Spacious house, newly built with a private outdoor pool in the beautiful Florida Keys. This is the perfect location for boating enthusiasts. There is space for both parking and boat trailers. An exclusive ramp is a block away (30-second drive or 1-minute walk), leads to Gulf of Mexico, and 10 minutes to the Atlantic Ocean. A pool heater is provided for free for renters during the Winter. Outdoor pool shower included. Barbecue gas always provided. Games include corn hole, domino, billard.

Guest favorite

A modern two-story building is situated next to a tranquil pool area. Lounge chairs are arranged around the pool, and thatched umbrellas provide shade. The upper balcony features a sitting area, enhancing the outdoor space, while tropical landscaping surrounds the property.

Home in Marathon

5 out of 5 average rating, 34 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Superhost

A scenic pool area is visible, featuring a hot tub adjacent to the water's edge. Palm trees sway gently in the breeze, providing a tropical atmosphere. The blue sky reflects on the tranquil water, enhancing the serene setting.

Home in Marathon

4.75 out of 5 average rating, 24 reviews

Sunset Views, Pool and Dock

Beautiful two bedroom two bath single family home with pool and spa with dock right on the water! Enjoy the beautiful sunset and bay views from our dock, deck or pool! Bring your boat and bathing suits and enjoy this wonderful home in the Heart of the Florida Keys! Pool heat is an additional fee Kayaks and golf carts rental available upon request Saturday to Saturday during busy months except September and October. And you can always ask 7 night minimum no exceptions VACA-22-34

Guest favorite

Home in Marathon

4.89 out of 5 average rating, 73 reviews

Dream Vacation KCB Marathon with private pool !

Dream Vacation Duplex in Key Colony Beach. Private pool Brand New state of the art house with all commodities and amenities, 3 bicycles 2 kayaks near to restaurants, fast WIFI, washer ,dryer, blue tooth speakers, night mood lights. A modern lift for boat up to 18000 lb Main canal Use of electric golf car Gem and jet sky and boat can be arrange Electric Gem-4 car offered for a minimum extra charge Options of private boat or jet sky (ask) Heated pool on demand (extra cost)

Guest favorite

A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.

Cottage in Islamorada

4.96 out of 5 average rating, 110 reviews

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

Top guest favorite

A private backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned on the wooden deck beside the pool. The two-story home includes large glass doors that open onto the deck, providing easy access to outdoor spaces.

Home in Duck Key

5 out of 5 average rating, 70 reviews

Private Pool Tropical Oasis - Centrally Located

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

Guest favorite

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

4.96 out of 5 average rating, 112 reviews

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

Superhost

Home in Key Colony Beach

4.9 out of 5 average rating, 10 reviews

Waterfront Luxury Home with Pool and Boat Dock

Waterfront paradise in the community of Key Colony in Marathon. Completely renovated and upgraded. Spacious kitchen with a large dining area. A screened porch overlooking the heated pool offers lounge seating and outdoor dining. Enjoy a refreshing drink at your private pool and grill your fresh catch in the outdoor kitchen. A private boat slip accommodates a boat up to 38 feet and includes a fish cleaning station, free water and shore power.