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Vacation rentals with a kayak in Big Pine Key

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Big Pine Key kayak rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a kayak

Guest favorite
Four kayaks are neatly stacked against a white fence, with green turf laid beneath them. Nearby, a boat lift is visible along the water, framed by tropical palm trees under a clear blue sky.
Home in Marathon
4.95 out of 5 average rating, 131 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

Superhost
A spacious deck is featured with several comfortable seating options overlooking tranquil waters. Lush greenery lines the opposite shore, providing a serene backdrop. Bright skies create an inviting atmosphere, highlighting the direct waterfront access and outdoor living potential.
Home in Marathon
4.8 out of 5 average rating, 35 reviews

Luxury Waterfront Retreat with Dockage & Pool

Superhost
A spacious living area features comfortable seating arrangements with two leather sofas facing a decorative area rug. The open-concept design connects to a dining space and a fully equipped kitchen, all accented by natural light from multiple windows.
Home in Marathon
5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

Superhost
A wooden deck extends over the water, featuring two lounge chairs oriented towards the ocean. A barbecue grill is positioned nearby, with lush greenery framing the scene. The clear blue water and bright sky create a serene backdrop.
Home in Marathon
4.86 out of 5 average rating, 7 reviews

Dolfan Oceanfront Cottage Direct oceanfront with 5

Superhost
A comfortable living area is showcased with a dark leather sofa and a rustic coffee table set on a patterned rug. Large windows offer views of the canal, while modern decor and a ceiling fan enhance the inviting atmosphere.
Home in Cudjoe Key
4.8 out of 5 average rating, 20 reviews

Keys Time #437 - Cudjoe Key, Oceanfront Community

Guest favorite
A dining area features a glass-top table surrounded by four woven chairs. Light flows in from nearby doors, illuminating the open layout that connects to a welcoming living space. Wall-mounted decor and book shelves add another layer of character.
Home in Marathon
4.94 out of 5 average rating, 32 reviews

Waterfront w/pool and hot tub

Guest favorite
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

Guest favorite
An open living area is highlighted by wooden ceilings and light-colored walls. A spacious sectional sofa with decorative pillows is positioned near a television. An inviting coffee table sits in front, with a dining area visible to the side, featuring a set of elegant white chairs and a wooden table.
Home in Key Colony Beach
4.87 out of 5 average rating, 15 reviews

Fun in the Sun!

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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.
Cottage in Cudjoe Key
4.81 out of 5 average rating, 95 reviews

OCEANIA... water front cottage retreat ~

Guest favorite
Two stand-up paddleboards are stored on a rack beside a white wall, surrounded by gravel. Lush green palm trees provide a tropical backdrop, and a soft light filters through the outdoor area.
Cottage in Islamorada
4.96 out of 5 average rating, 79 reviews

Islamorada bungalow 2 bed & pool

Superhost
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.
Cottage in Cudjoe Key
New place to stay

Ocean Breeze at Venture Out 537

Superhost
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.
Cottage in Cudjoe Key
4.7 out of 5 average rating, 145 reviews

Calypso Cottage

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.
Cottage in Key Colony Beach
5 out of 5 average rating, 10 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

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Quick stats about vacation rentals with a kayak in Big Pine Key

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$25,105 GYD before taxes and fees

  • Total number of reviews

    240 reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore