Big Pine Key vacation rentals
Book unique vacation rentals, houses, 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
Big Pine Key house rentals
Home in Key Colony Beach
4.91 out of 5 average rating, 117 reviewsThe Snapper House 3/2.5 45' dock sleeps 8+ pets OK
Home in Key West
4.95 out of 5 average rating, 276 reviewsRomantic Retreat - 2 person K Suite, Pvt deck/Spa!
Home in Key Colony Beach
4.81 out of 5 average rating, 134 reviewsWaterview from three sides, Cabana Club, 30' Docks
Home in Cudjoe Key
4.81 out of 5 average rating, 225 reviewsOCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Home in Marathon
5.0 out of 5 average rating, 4 reviewsP31 - 11785 5th Ave. Ocean
Home in Marathon
5.0 out of 5 average rating, 16 reviewsFlorida Keys Oceanside Utopia
Home in Marathon
4.97 out of 5 average rating, 36 reviewsThe Gulf Cottage at Marathon Key
Home in Marathon
4.97 out of 5 average rating, 35 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Big Pine Key cabin rentals
Cabin in Marathon
4.91 out of 5 average rating, 32 reviewsNew Cabins at Bonefish Bay
Cabin in Marathon
4.9 out of 5 average rating, 61 reviewsConch Key Cottages with Sailboat
Cabin in Key West
4.88 out of 5 average rating, 8 reviewsLiving life Dockside
Cabin in Big Pine Key
4.79 out of 5 average rating, 53 reviews2 Bedroom Pink Cabin Half/Duplex # 11
Cabin in Key West
4.57 out of 5 average rating, 143 reviewsLovely 2BR | Pool | Patio | W/D
Cabin in Cudjoe Key
New place to stay85 Canalfront Empty RV Lot with 35' Seawall
Cabin in Marathon
4.46 out of 5 average rating, 87 reviewsTropical Cottages - Cottage # 05
Place to stay in Marathon
4.54 out of 5 average rating, 13 reviewsViamarhe Cabin-Private beach, Kayak, yard games
Big Pine Key cottage rentals
Cottage in Islamorada
4.84 out of 5 average rating, 133 reviews1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Cottage in Key Largo
4.89 out of 5 average rating, 274 reviewsCottage By The Sea
Cottage in Cudjoe Key
4.92 out of 5 average rating, 83 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Cottage in Marathon
4.96 out of 5 average rating, 23 reviewsCatch n' Relax Canalfront Cottage in Marathon
Cottage in Islamorada
4.95 out of 5 average rating, 43 reviewsIslamorada bungalow 2 bed & pool
Cottage in Cudjoe Key
4.84 out of 5 average rating, 32 reviewsTidewater Views @ Venture Out - Waterfront
Cottage in Islamorada
4.94 out of 5 average rating, 16 reviewsWaterfront Cottage Walk to World Famous Lorelei
Cottage in Islamorada
4.97 out of 5 average rating, 70 reviewsKey Lime Cottage 2br 1ba w/pool
Quick stats about vacation rentals in Big Pine Key
Total rentals
230 properties
Rentals with a pool
100 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
190 properties are a good fit for families
Total number of reviews
4.4K reviews
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
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 110 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Big Pine Key?
Experience the best of Big Pine Key with our house rentals, starting at about $60 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 60 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 40 house rentals with self check-in in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Big Pine Key have wifi?
Absolutely! We offer over 160 house rentals with wifi in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
Are there Big Pine Key house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 house 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 150 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Big Pine Key?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with self check-in, over 60 homes with a bbq area, over 160 homes with wifi, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
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