10 Best Airbnb Vacation Rentals In Big Pine Key, Florida - Updated 2024

Ashi
Ashi  
Updated
| 4 min read

Lose yourself in the tranquility and natural wonders of Big Pine Key and make memories that last a lifetime. National Key Deer Refuge, home to the remarkable Key Deer, stretches over 9,200 acres (3,723.11 hectares) and is a treat for explorers of natural beauty. The entire area is covered by pine and rock forests, freshwater wetlands, salt marsh wetlands, and mangrove forests, along with 23 endangered species of plants and animals. Additionally, Blue Hole, the only freshwater lake in the Florida Keys, promises up-close views of Key deer, turtles, and even crocodiles. If you are looking to spend a night under the stars, Bahia Honda State Park is an excellent choice with its numerous campsites and beaches. Choose a cozy rental and experience all of the above wonders in complete privacy. Read on to find a list of the best Airbnb vacation rentals in Big Pine Key, Florida.

We handpicked these listings carefully, considering (wherever possible) Superhost status. recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 08, 2024.

1. Charming houseboat with access to a pool (from USD 199)

Located in Old Wooden Bridge Guest Cottages & Marina this houseboat will give you access to the resort’s luxurious facilities. Take a dip in the beautiful saltwater pool or take advantage of the convenient fish-cleaning facilities for your fresh catch. If you have a boat, feel free to bring it or rent it from the resort for an additional fee.

The houseboat provides guests with a well-equipped kitchen designed to fulfill all their culinary needs. There is also Wi-Fi access and air conditioning for added convenience.

Stayed at this property?
Big Pine Key, Florida, United States
48.6 km (30.2 mi) from The Hemingway Home and Museum
131 reviews   Wifi Available
Houseboat 2 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Cleanliness:
the place was very clean
the house boat was very clean and built with meticulous detail
awesome experience great location and cleanliness is on point
Host:
office staff had everything i could ask for and were very helpful
the management was very friendly and helpful and offered a number of useful local tips
the people that work there are friendly and helpful recommend some great food spots
lots of wild friendly deer and lizards too
the bridge yields excellent fishing (especially at night) and the staff are all so nice and helpful
Location:
perfect location for all we wanted to do
but for me the location greatly exceeded my expectations and the plus is succeeded the minuses
perfect location with easy access to key west local eateries and right on the bay minutes from the ocean
aqualodges at owb marina are a great location for boating and kayaking in the northern keys
Read more reviews

2. Blue Breeze (from USD 412)

This spectacular property is just steps away from open water, offering breathtaking views of the ocean. The highlight of this home is the concrete dock, which offers immediate access to the water, perfect for boating enthusiasts.

To meet your needs, the house has a dedicated office space, allowing you to deal with work-related tasks. Stay connected with your loved ones or catch up on your favorite activities via the Wi-Fi. Further, the property also has a garden - perfect for leisurely strolls.

Stayed at this property?
Big Pine Key, Florida, United States
48.36 km (30.1 mi) from The Hemingway Home and Museum
56 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Cleanliness:
house is clean and has everything you need
Location:
house was a great place to spend some time
Read more reviews

3. Beautiful houseboat with Wi-Fi (from USD 194)

This beautiful houseboat has a fully equipped kitchen and a comfortable living room with everything you need to enjoy yourself. For your entertainment and convenience, this accommodation has a television and Wi-Fi. For your swimming pleasure, the host offers access to a shared saltwater pool, where you can relax and unwind. Do note that swimming is not permitted in the marina boat basin for safety reasons.

The rental allows pets as well. Make sure to inform the host in advance if you are planning on bringing along your furry friend.

Stayed at this property?
Big Pine Key, Florida, United States
48.59 km (30.2 mi) from The Hemingway Home and Museum
121 reviews   Wifi Available
Houseboat 1 Bed 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the room was fantastic
Host:
robin is a great host
Read more reviews

4. Lavish home with a hot tub (from USD 4500)

This luxurious home offers the perfect retreat where you can relax and take in the beauty of the Florida Keys. The master suite is equipped with a hot tub where you can soak in a soothing bath. The living space comes with a stunning 82-inch TV with cable access, and reliable Wi-Fi to keep you connected.

To ensure a seamless experience, the property has an on-site housekeeper available to assist you during your time here. Please note that the place is available for long-term rentals only.

Stayed at this property?
Big Pine Key, Florida, United States
45.74 km (28.5 mi) from The Hemingway Home and Museum
3 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Cleanliness:
very nice and clean place
Location:
very peaceful and relaxing location and it has the biggest television i've ever seen
Read more reviews

5. Spacious home with air conditioning (from USD 163)

This charming stilt house faces the calm waters of the canal making it a peaceful escape in Big Pine Key. The house is equipped with air conditioning along with ceiling fans, offering a comfortable stay even on the hottest of days.

For those who enjoy the outdoors, the property is close to several fun-filled activities including fishing, hiking, biking, and kayaking.

Stayed at this property?
Big Pine Key, Florida, United States
48.05 km (29.9 mi) from The Hemingway Home and Museum
22 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
the air worked great and the beds were very comfortable
Cleanliness:
the house was very clean and comfortable
it was spacious clean and quiet
Host:
there was so much to do and the host was wonderful
Location:
the location is great
the location is perfect
great neighborhood to bike and walk
we absolutely love the house and location
the house was great and the location perfect
Read more reviews

6. Stylish home with a dock (from USD 175)

This well-designed rental has an open floor plan that seamlessly integrates the fully equipped kitchen and a large island. The dining room opens out onto the back deck, embracing the outdoor beauty of the surroundings. The property also comes with a spacious dock, minutes from the open water.

Other amenities include free on-site parking and laundry facilities.

Stayed at this property?
Big Pine Key, Florida, United States
45.48 km (28.3 mi) from The Hemingway Home and Museum
10 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the home does have strong internet and has roku tvs throughout
Cleanliness:
the home feels bigger than it looks and was extremely clean upon our arrival
overall we were extremely happy with the location experience cleanliness and value of our stay
Host:
the owners of the home are also very responsive and take fantastic care of the home
everything worked as advertised and alfred is a great responsive host
Location:
beautiful and all around great place to stay
Read more reviews

7. The Hideaway (from USD 410)

This beautiful home located on a spacious lot offers plenty of room for privacy and relaxation. If you are a boating enthusiast, you will be happy that a boat ramp is conveniently located less than 5 minutes from the rental. In addition, there is plenty of space on the property to park your boat safely.

The property allows a maximum of two dogs. Do note that the dogs must be on a leash when outside the property. It is also important for guests to clean up after their dogs.

Stayed at this property?
Big Pine Key, Florida, United States
48.4 km (30.1 mi) from The Hemingway Home and Museum
75 reviews   Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
we especially liked the outdoor deck table and chairs
a fun house with a large sofa and kitchen and bedding that were comfortable to use
very nice interior space comfortable for our family visit
the kitchen was nice with new appliances
we stayed with 6 people and there was more than enough room for us all to be comfortable
Cleanliness:
nice and clean home with plenty of space
excellent the house was beautiful clean modern and very spacious
the beds are super comfortable & it was very clean
house was spacious and clean
and the place was overall clean
Host:
hosts were extremely responsive when we asked any questions
the hosts provided great hospitality and communication
i highly recommend using this host for any rentals
truly an enjoyable space and great service from the owners
the host made sure to communicate everything with me & was very thorough with their communication
Location:
good location between key west and marathon
location is great winn dixie is very close
good location to access the middle and southern keys
this location and home are great
it’s a pretty remote location and about 35-45 mins to key west
Read more reviews

8. Comfortable home with access to a pool (from USD 228)

This adorable tiny home is conveniently located next to a shared pool, allowing guests access to this delightful facility. There is also an outdoor terrace, adorned with plush rattan sofas and armchairs. For those looking to enjoy the outdoors, bikes and kayaks are provided on request. The rental also includes a laundry facility and a barbecue grill.

The dedicated workspace and Wi-Fi access allow guests to work remotely. Moreover, free driveway parking is available.

Stayed at this property?
Big Pine Key, Florida, United States
45.95 km (28.6 mi) from The Hemingway Home and Museum
84 reviews   Wifi Available
Tiny home 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
we had a very comfortable stay
Cleanliness:
very clean comfortable and safe
now clean place well maintained and next to a pool
the place was nice and clean
the house was comfortable and clean
the place itself is beautifully clean and peaceful - perfect for our family of four
Host:
friendly hosts i felt very welcomed and great communication
the price was right compared to hotels on key west hosts alex and vikki are excellent
Location:
the location was close to restaurants stations and the main attractions
great tiny house in a cute rv park we loved our stay
it was in a trailer park and all the neighbors were friendly
easily walkable to locally recommend restaurant and grocery store
great little place to stay right in between everything fun in the keys
Read more reviews

9. Inviting camper with a complete kitchen (from USD 110)

This delightful camper is surrounded by peaceful forests, giving you ample chance to enjoy views of wild deer and beautiful peacocks. Inside, you will find a fully equipped kitchen complete with a microwave, toaster, and coffee maker.

Further, high-speed internet access and satellite TV are provided for your convenience. In the evening, you can enjoy a drink in the outdoor sitting area.

Stayed at this property?
Big Pine Key, Florida, United States
47.26 km (29.4 mi) from The Hemingway Home and Museum
362 reviews   Superhost Wifi Available
Camper/RV 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
tv is great and good wifi
the a/c worked great the water for showers is hot and water pressure is good
the bed wasn't the greatest but it wasn't bad at all
bed is extremely comfortable
a great alternative to a hotel with noisy people staying in the room next to you
Cleanliness:
place was clean and as advertised
very clean and well equipped
it is clean and inviting
communication was great and the place was really clean
place is clean and comphy
Host:
gabriele is an awesome host
host was extremely helpful and friendly during checkin
she is a great host and she provided everything you would need for a comfy stay
what an amazing place and a really thoughtful host
this was our second stay with gabriele on big pine key she is very kind and hospitable
Location:
situated in a great location if you want to be close to civilization but not too close
v great location for star watching too
set in a quiet and peaceful location
we loved our stay here great location on a beautiful key
the location was perfect because we wanted to see the middle and southern keys
Read more reviews

10. Waterfront home with a spacious dock (from USD 700)

This stunning waterfront property offers boating enthusiasts direct access to the open water and a dock. It is the perfect spot for fishing and lobstering. For the adventurous, canoe and kayak rentals are within walking distance, making it easy to explore the surrounding waters.

Relax on the enclosed back porch, or soak up the sun on the private patio. All the bedrooms feature a memory foam mattress, allowing you to fully enjoy a peaceful night’s sleep.

Stayed at this property?
Big Pine Key, Florida, United States
48.6 km (30.2 mi) from The Hemingway Home and Museum
25 reviews   Wifi Available
ENTIRE HOME 6 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Cleanliness:
everything was clean and comfortable
great place to stay if you like privacy and peace and quiet clean and comfortable
we had a great time in this clean and comfortable home on big pine key
Host:
the host was absolutely fantastic
owners are making smart decisions with their updates
thank you for hosting us
lovely host and home natalie was great at communicating check-in instructions
natalie and and the owner were absolutely amazing by checking in frequently to ensure all was well
Location:
it was in a very good location
great place to stay within a short distance from key west
this is a great place super cute and right by the no name pub
the location is so quiet and peaceful which is everything one would need for a much needed getaway
beds were very comfortable we also loved walking to the no name pub just a few steps away
Read more reviews

Enjoy the sunshine of Florida in Big Pine Key

Big Pine Key offers tourists every ingredient required for the perfect vacation, including untouched wilderness, water sports, and pristine beaches. Choose an accommodation from the list above to rejuvenate and recharge your mind and body.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Ashi, a Literature post-graduate, has a fondness for reading, writing, and animals.

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