
Vacation rentals in Big Pine Key
Book unique cabins, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Big Pine Key
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Big Pine Key vacation rentals
Cabin rentals in Big Pine Key

Downtown 2BR Dog Friendly | Hot Tub | Deck
Clean, comfortable cottage in easy walking distance to Key West sites. A/C units kept rooms comfortable and the place was well equipped. Enjoyed our stay.

Viamarhe Cabin-Private beach, Kayak, yard games
We stayed for a week and loved our stay, the location was perfect for getting to all the places we wanted to see, the amenities we’re great for being able to make food at the B&B, we enjoyed the view and sitting in the hammock. Beautiful place. If you go walking the ocean recommend staying away from the resort on the left-hand side of the property due to they’re being sinking sand over there.

2 Bedroom Turquoise Cabin
Fantastic stay for the price. Very peaceful place and the staff on property were very kind. The house itself was great. Robin gave us some great recommendations for things to try around the area.

2/1 Two Bedroom and 1 Bath
Everyone was so nice and answer any concerns that I had even though I was late to check in it didn’t matter to them they got me settled right in I wouldn’t take no chances going to any other places when I come to visit again I thank you guys for making my trip stress free

2 Bedroom Pink Cabin Half/Duplex # 11
Enjoyed our stay!

Tropical Cottages - Cottage # 05
My husband and I stayed for 3 nights, and we brought our dogs. We had a fabulous time and loved the Tropical Cottages! Clean, cute, and had everything we needed. Very dog friendly as advertised. Great location too. The tiki bar and taco truck are added bonuses. I would definitely book here again and recommend to friends, with or without their pups!

1 Bedroom Cabin Half/Duplex Unit B up on Stilts
We will definitely be back. Great location to many attractions. Robin was a great host. Very responsive.

2 Bedroom Pink Cabin Half/Duplex # 10
Robin and Tiffany were great, they were very responsive and helpful!
Condo rentals in Big Pine Key

Rooftop Penthouse
The stay was perfect for me and my friends to experience Key West! Being right on Duval made it easy to walk to all the restaurants and bars in the area.

Tropical Escape at Sunrise
We enjoyed our stay! A little outside of the heart of Key West so it was very quiet. This place does have a unit above, luckily we were not bothered by any sort of upstairs noise. Would recommend!

A Perfect Getaway
Loved the gated community, very quiet, no through traffic. The pool was very nice and clean. The condo was close to restaurants and the park with a great beach. I loved the area and would love to return someday.

Fully renovated 2/2 bath condo w/ shared pool!
Enjoyed our time at Chris’s place. Plenty of towels and the kitchen was well furnished. Wonder if an air purifier might help as a few of our allergies kicked in when we were inside. All in all a great vacation

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage
The condo is beautiful and close to everything! We had plenty of room for the whole family.

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.

Beachside Unit 28 - Private Beach, Pool & Paradise
My Daughter and her newlywed husband spent their honeymoon here and all they could talk about is how perfect the place is. They never wanted to leave! Everytime I spoke to her and asked her about the place she had nothing but good things to say. She loved how peaceful it was and how she could walk right out the door and a few steps from the water. Oh and the Starbucks there is the cutest one around. They plan to come back for anniversary’s. Heck what I saw on FaceTime, I might even pay this place a visit. Thank you for making my Daughters honeymoon one to remember!

Sombrero Beach Tropical Getaway
This was our 2nd stay at this place. We love all the resort has to offer and the location makes it easy to get to places in Marathon
Cottage rentals in Big Pine Key

Turtle Cove Views at Venture Out
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.

Islamorada bungalow 2 bed & pool
Such a warm, quaint place. Clean, right next to the pool and close to nearby restaurants, activities and much more. Loved it.

Waterfront Cottage Walk to World Famous Lorelei
What an amazing place! My wife and I have stayed in Airbnb properties all over the world, and this was one of our favorites. Exactly as described. Very clean, safe, and comfortable. The location and layout of the property is absolutely perfect and private. This was our first time to Islamorada and this place made it an even better experience. We had a manatee sighting and the deck over the water was my favorite part. Perfect place to have a drink and watch the sunset. If you are planning a trip to the keys, do yourself a favor and stay here.

Ocean Breeze at Venture Out 537
I had a wonderful stay at this Airbnb! The home was perfect for our occasion—just as advertised, and even more charming in person. The vibrant and inviting colors gave the space a warm, welcoming feel. There was a slight delay with check-in, but our host, John, responded quickly and resolved the issue right away, which we really appreciated. We also took full advantage of the amenities, which added to the overall experience. Everything was clean, comfortable, and well thought out. I would definitely stay here again and highly recommend it to others!

Catch n' Relax Canalfront Cottage in Marathon
We really enjoyed our stay at Wendy's place! It was clean, comfortable, and had everything we needed for our stay. We enjoyed riding the bikes to Seven Mile Bridge and exploring with the kayaks. Would definitely recommend it!

Namaste: A blissful one bedroom cottage
This was, by far, the best Airbnb I’ve ever stayed at, and I’ve been at Airbnb’s since 2012. It was the perfect place for our honeymoon stay, very VERY easy walk to Duval (under 2 minutes to Sloppy Joe’s). Seriously, this place is IT.

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Jason’s place was a great place to stay in the keys!! Jason is great at responding great location, clean house only the couch could use a cleaning. It would have been nice if there were trash bags, extra hand soap and extra toilet paper. Other then that it was perfect!!

Calypso Cottage
Everything was perfect! I loved the screened in front porch! We spent a lot of time out there and the back was so peaceful for watching the sun come up with my morning cup of coffee. The staff at the resort were super friendly and helpful and I notice security was constantly driving around which made it feel safe and taken care of. Everyone at the resort looked so happy and relaxed! The pool!!! I didn’t want to leave and it has great hours! We were able to explore the area and still had time to go swimming at the pool…under the stars! It was a wonderful experience. Plan to some time go back and plan the whole trip staying there!
Quick stats about vacation rentals in Big Pine Key
Total rentals
260 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
4.9K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
130 properties have a pool
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Big Pine Key?
Yes! Work meets play with ease at over 90 vacation rentals in Big Pine Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Big Pine Key?
Four-legged friends are welcome in Big Pine Key. Choose from more than 120 vacation rentals for guests traveling with pets.
How much does it cost to stay in rv rentals in Big Pine Key?
Experience the best of Big Pine Key with our rv rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Big Pine Key have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Big Pine Key have a gym?
Absolutely! We offer over 10 house rentals with a gym in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Big Pine Key have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Are there Big Pine Key rv rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 rv rentals with pools in Big Pine Key, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Big Pine Key?
Big Pine Key has more than 160 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
- Key West Vacation rentals
- Florida Keys Vacation rentals
- Miami Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Central Florida Vacation rentals
- Seminole Vacation rentals
- Tampa Vacation rentals
- Apartment rentals Big Pine Key
- Beachfront rentals Big Pine Key
- Rentals with a hot tub Big Pine Key
- Kid-friendly rentals Big Pine Key
- Rentals with a patio Big Pine Key
- Waterfront rentals Big Pine Key
- Cottage rentals Big Pine Key
- Fitness-friendly rentals Big Pine Key
- Smoking-friendly rentals Big Pine Key
- Rentals with pools Big Pine Key
- Villa rentals Big Pine Key
- Rentals with a fire pit Big Pine Key
- Pet-friendly rentals Big Pine Key
- House rentals Big Pine Key
- Rentals with beach access Big Pine Key
- Rentals with a washer and dryer Big Pine Key
- Rentals with outdoor seating Big Pine Key
- Rentals with a kayak Big Pine Key
- Family-friendly rentals Big Pine Key
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom