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 October 24, 2025.
1. Charming houseboat with access to a pool (from USD 320)
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.
Big Pine Key, Florida, United States
48.6 km (30.2 mi) from The Hemingway Home and MuseumSuperhost
Accommodates: 6
Top guest reviews
Host:
office staff had everything i could ask for and were very helpfulthe management was very friendly and helpful and offered a number of useful local tipsthe people that work there are friendly and helpful recommend some great food spotslots of wild friendly deer and lizards toothe bridge yields excellent fishing (especially at night) and the staff are all so nice and helpfulLocation:
perfect location for all we wanted to dobut for me the location greatly exceeded my expectations and the plus is succeeded the minusesperfect location with easy access to key west local eateries and right on the bay minutes from the oceanaqualodges at owb marina are a great location for boating and kayaking in the northern keysRead more reviewsCleanliness:
the place was very cleanthe house boat was very clean and built with meticulous detailawesome experience great location and cleanliness is on point
2. Blue Breeze (from USD 5349)
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.
Big Pine Key, Florida, United States
48.36 km (30.1 mi) from The Hemingway Home and MuseumAccommodates: 8
Top guest reviews
Location:
house was a great place to spend some timeRead more reviewsCleanliness:
house is clean and has everything you need
3. Beautiful houseboat with Wi-Fi (from USD 268)
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.
Big Pine Key, Florida, United States
48.59 km (30.2 mi) from The Hemingway Home and MuseumAccommodates: 4
Top guest reviews
Host:
robin is a great hostRead more reviewsAmenities & Room:
the room was fantastic
4. Lavish home with a hot tub (from USD 151685)
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.
Big Pine Key, Florida, United States
45.74 km (28.5 mi) from The Hemingway Home and MuseumAccommodates: 8
Top guest reviews
Location:
very peaceful and relaxing location and it has the biggest television i've ever seenRead more reviewsCleanliness:
very nice and clean place
5. Spacious home with air conditioning (from USD 5353)
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.
Big Pine Key, Florida, United States
48.05 km (29.9 mi) from The Hemingway Home and MuseumAccommodates: 10
Top guest reviews
Host:
there was so much to do and the host was wonderfulLocation:
the location is greatthe location is perfectgreat neighborhood to bike and walkwe absolutely love the house and locationthe house was great and the location perfectRead more reviewsAmenities & Room:
the air worked great and the beds were very comfortable
6. Stylish home with a dock (from USD 1672)
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.
Big Pine Key, Florida, United States
45.48 km (28.3 mi) from The Hemingway Home and MuseumAccommodates: 8
Top guest reviews
Host:
the owners of the home are also very responsive and take fantastic care of the homeeverything worked as advertised and alfred is a great responsive hostLocation:
beautiful and all around great place to stayCleanliness:
the home feels bigger than it looks and was extremely clean upon our arrivaloverall we were extremely happy with the location experience cleanliness and value of our stayRead more reviewsAmenities & Room:
the home does have strong internet and has roku tvs throughout
7. The Hideaway (from USD 1453)
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.
Big Pine Key, Florida, United States
48.4 km (30.1 mi) from The Hemingway Home and MuseumAccommodates: 6
Top guest reviews
Host:
hosts were extremely responsive when we asked any questionsthe hosts provided great hospitality and communicationi highly recommend using this host for any rentalstruly an enjoyable space and great service from the ownersthe host made sure to communicate everything with me & was very thorough with their communicationLocation:
good location between key west and marathonlocation is great winn dixie is very closegood location to access the middle and southern keysthis location and home are greatit’s a pretty remote location and about 35-45 mins to key westCleanliness:
nice and clean home with plenty of spaceexcellent the house was beautiful clean modern and very spaciousthe beds are super comfortable & it was very cleanhouse was spacious and cleanand the place was overall cleanRead more reviewsAmenities & Room:
we especially liked the outdoor deck table and chairsa fun house with a large sofa and kitchen and bedding that were comfortable to usevery nice interior space comfortable for our family visitthe kitchen was nice with new applianceswe stayed with 6 people and there was more than enough room for us all to be comfortable
8. Comfortable home with access to a pool (from USD 303)
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.
Big Pine Key, Florida, United States
45.95 km (28.6 mi) from The Hemingway Home and MuseumAccommodates: 4
Top guest reviews
Host:
friendly hosts i felt very welcomed and great communicationthe price was right compared to hotels on key west hosts alex and vikki are excellentLocation:
the location was close to restaurants stations and the main attractionsgreat tiny house in a cute rv park we loved our stayit was in a trailer park and all the neighbors were friendlyeasily walkable to locally recommend restaurant and grocery storegreat little place to stay right in between everything fun in the keysCleanliness:
very clean comfortable and safenow clean place well maintained and next to a poolthe place was nice and cleanthe house was comfortable and cleanthe place itself is beautifully clean and peaceful - perfect for our family of fourRead more reviewsAmenities & Room:
we had a very comfortable stay
9. Inviting camper with a complete kitchen (from USD 88)
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.
Big Pine Key, Florida, United States
47.26 km (29.4 mi) from The Hemingway Home and MuseumAccommodates: 2
Top guest reviews
Host:
gabriele is an awesome hosthost was extremely helpful and friendly during checkinshe is a great host and she provided everything you would need for a comfy staywhat an amazing place and a really thoughtful hostthis was our second stay with gabriele on big pine key she is very kind and hospitableLocation:
situated in a great location if you want to be close to civilization but not too closev great location for star watching tooset in a quiet and peaceful locationwe loved our stay here great location on a beautiful keythe location was perfect because we wanted to see the middle and southern keysCleanliness:
place was clean and as advertisedvery clean and well equippedit is clean and invitingcommunication was great and the place was really cleanplace is clean and comphyRead more reviewsAmenities & Room:
tv is great and good wifithe a/c worked great the water for showers is hot and water pressure is goodthe bed wasn't the greatest but it wasn't bad at allbed is extremely comfortablea great alternative to a hotel with noisy people staying in the room next to you
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.
Big Pine Key, Florida, United States
48.6 km (30.2 mi) from The Hemingway Home and MuseumAccommodates: 10
Top guest reviews
Host:
the host was absolutely fantasticowners are making smart decisions with their updatesthank you for hosting uslovely host and home natalie was great at communicating check-in instructionsnatalie and and the owner were absolutely amazing by checking in frequently to ensure all was wellLocation:
it was in a very good locationgreat place to stay within a short distance from key westthis is a great place super cute and right by the no name pubthe location is so quiet and peaceful which is everything one would need for a much needed getawaybeds were very comfortable we also loved walking to the no name pub just a few steps awayRead more reviewsCleanliness:
everything was clean and comfortablegreat place to stay if you like privacy and peace and quiet clean and comfortablewe had a great time in this clean and comfortable home on big pine key
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.
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