Vacation rentals in Big Pine

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Top-rated vacation rentals in Big Pine

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Guest favorite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 127 reviews

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

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Superhost

Tiny home in Big Pine Key

4.81 out of 5 average rating, 190 reviews

Cheerful Tiny House in the Florida Keys

Enjoy your trip to the keys by staying at this wonderful tiny house, surrounded by nature and deers! This is a hidden gem in the keys for your relaxation, enjoyment. Cozy and roomy space for the whole family! The Tiny house is located in the small Breezy Pines RV Resort. It has everything you would need during your trip. Outdoor patio area with rattan sofa and armchairs, grill offer an additional comfort for incredible vacation! it has everything for your nice and comfy stay close to Key West!

Guest favorite

A compact vehicle is parked on a gravel lot between two trailers, showcasing their unique exteriors. The sky is bright with a few fluffy clouds, and palm trees add a touch of greenery to the surroundings. The area is designed for easy access and convenience.

Camper/RV in Big Pine Key

4.91 out of 5 average rating, 11 reviews

Perfect Couple Oasis!

You’ll treasure your time at this memorable location. New camper recently added to lot. Queen bedroom, bathroom, open living room with a full kitchen. Located on Big Pine Key, FL, between Marathon and Key West. Parking for 1 vehicle on lot, large vehicles will not fit. Key deer and roosters walk around park. Community pool and laundry facility. Great place to relax after fun in the sun or a night on the town! Renters must 25 years old or over. Community requires a rental form to be completed.

Guest favorite

A modern washing machine is showcased beside a stainless steel countertop. A glass container labeled 'Homemade Laundry Soap' is placed nearby. Natural light filters through sheer curtains, enhancing the functional space.

Tiny home in Big Pine Key

4.93 out of 5 average rating, 75 reviews

Tiny Fish Haus

Come experience Tiny Home Living in this Park Model RV right next to the National Key Deer Refuge! . Relax on our covered patio next to a large Saltwater Swimming Pool, Cook dinner on a Blackstone grill , enjoy WIFI, Games, a Flat Screen TV , we have Premium Organic Bedding on our Queen beds for comfort. Turkish Towels for bath and beach..explore Big Pine Key with our 2 bicycles that are included .AirPurifier for clean air inside. 28 Miles to Key West. Keys Shuttle located next to our park

Top guest favorite

A wooden dock extends over calm waters, flanked by white pilings and gently swaying palm trees. The warm hues of twilight fill the sky, reflecting softly on the water's surface, creating a serene atmosphere perfect for evening relaxation.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 106 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!

Superhost

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

4.79 out of 5 average rating, 265 reviews

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

Superhost

Home in Little Torch Key

4.79 out of 5 average rating, 14 reviews

Indulge yourself. It's heavenly in Little Torch

Welcome to our new 3 bedroom, 2 full bath home with a 60' dock on a gorgeous wide deep water canal. We are only 1,200' to the open waters of Pine Channel at the very southern end of Little Torch Key. Our home is thoroughly cleaned and sanitized before each visit. We have a guest friendly cancellation policy described in the additional house rules section. The living room, dining area and spacious kitchen open to a cozy rear porch and deck overlooking the serene canal. Enjoy ---....

Guest favorite

Cottage in Little Torch Key

4.9 out of 5 average rating, 167 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!

Superhost

An outdoor dining area is illuminated by string lights, surrounded by vibrant tropical plants. A picnic table and several seating options create a welcoming space, while soft greenery covers the ground. Colorful decorative elements are present among the landscaping, enhancing the tranquil evening ambiance.

Camper/RV in Big Pine Key

4.84 out of 5 average rating, 64 reviews

The Island Gypsy

Reconnect with nature at this unforgettable escape. Property butts up to the endangered Key deer refuge with almost daily sightings in the yard. Only 6 miles offshore is Looe key and the 3rd largest reef in the world. Our lot has parking for 2 vehicles with a outdoor dining area and large backyard for hanging out. The island gypsy is our 5th wheel which sleeps 4 with a queen bed, queen bunk beds and a sofa bed. Heated pool in the park and right across street from clubhouse.

Guest favorite

Three colorful Adirondack chairs, yellow, turquoise, and green, are positioned on a sandy beach facing a calm blue ocean. A rocky shore and sparse greenery surround the seating area, while fluffy white clouds drift in a bright sky, enhancing the serene water view.

Villa in Marathon

4.91 out of 5 average rating, 310 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 158 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.

Top guest favorite

A view from the balcony captures neighboring houses and a landscaped area, with palm trees visible below. The calm waters of the Atlantic ocean stretch in the background under a clear, blue sky. The white railing frames the scenic vista.

Home in Cudjoe Key

4.93 out of 5 average rating, 177 reviews

Cudjoe Bay- Newly Renovated Oceanviews with Pool

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."