Waterfront vacation rentals in Big Pine Key

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Big Pine Key

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Key Colony Beach

4.91 out of 5 average rating, 117 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).

Guest favorite

Home in Key Colony Beach

4.98 out of 5 average rating, 54 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 favorite

Condo in Key Colony Beach

4.97 out of 5 average rating, 175 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Guest favorite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Florida Keys Oceanside Utopia

Create amazing memories at this beautiful oceanside home in Marathon, FL. Relax in the backyard or outdoor bar, watching boats cruise by on the aqua waters of Vaca Cut. Enjoy a fully equipped, newly remodeled and furnished duplex, beautifully decorated and ready to be your home away from home. Our waterfront location can’t be beat. Marathon has everything you need for a vacation to do it all on one Key. We can’t wait for you to experience our vacation home. Must be 25+ years old to book.

Guest favorite

Cottage in Little Torch Key

4.91 out of 5 average rating, 147 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 85 reviews

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

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite 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. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

Guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 125 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 109 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill 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

Home in Marathon

4.9 out of 5 average rating, 137 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

Guest favorite

Home in Key Colony Beach

5.0 out of 5 average rating, 66 reviews

“La casa azul” step 3’ to a private pool

2 bedroom, 2 bath, 1/2 duplex on 9th St. Key Colony Beach. Located on a deep canal with a 37.5' dock and fish cleaning table. Immediate access to the ocean and gulf. This home provides all the essentials for cooking your catch of the day. Enjoy a private pool overlooking the canal with a heated or chilled pool. Master bedroom has a king size bed and en suite. Guest bedroom has a queen bed.

Guest favorite

Townhouse in Marathon

4.97 out of 5 average rating, 148 reviews

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house with hospital grade sanitizer.

Guest favorite

Home in Marathon

4.98 out of 5 average rating, 121 reviews

Marathon one-level home on the Marina - with slip!

***New Listing! Recently renovated with all new furnishings and appliances*** Beautiful oasis in the heart of the Florida Keys, Marathon is a fisherman's paradise. Coral Lagoon is the perfect destination for a relaxing family getaway and this home is all new with stylish interior and unbeatable location.