Big Pine Key vacation rentals
Book unique cottages, 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
Big Pine Key cottage rentals
Cottage in Islamorada
4.84 out of 5 average rating, 136 reviews1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Cottage in Key West
4.9 out of 5 average rating, 100 reviewsThe Dancing Rooster
Cottage in Marathon
4.96 out of 5 average rating, 23 reviewsCatch n' Relax Canalfront Cottage in Marathon
Cottage in Cudjoe Key
4.92 out of 5 average rating, 85 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Cottage in Islamorada
4.95 out of 5 average rating, 44 reviewsIslamorada bungalow 2 bed & pool
Cottage in Islamorada
4.94 out of 5 average rating, 16 reviewsWaterfront Cottage Walk to World Famous Lorelei
Cottage in Key West
4.88 out of 5 average rating, 33 reviewsNamaste: A blissful one bedroom cottage
Cottage in Islamorada
4.97 out of 5 average rating, 73 reviewsKey Lime Cottage 2br 1ba w/pool
Big Pine Key cabin rentals
Cabin in Marathon
4.92 out of 5 average rating, 37 reviewsNew Cabins at Bonefish Bay
Cabin in Marathon
4.9 out of 5 average rating, 62 reviewsConch Key Cottages with Sailboat
Cabin in Key West
4.8 out of 5 average rating, 10 reviewsLiving life Dockside
Cabin in Big Pine Key
4.78 out of 5 average rating, 55 reviews2 Bedroom Pink Cabin Half/Duplex # 11
Cabin in Key West
4.61 out of 5 average rating, 101 reviewsDowntown 2BR Dog Friendly | Hot Tub | Deck
Cabin in Marathon
4.5 out of 5 average rating, 171 reviewsTropical Cottages - Cottage # 7
Cabin in Cudjoe Key
New place to stay85 Canalfront Empty RV Lot with 35' Seawall
Place to stay in Marathon
4.57 out of 5 average rating, 14 reviewsViamarhe Cabin-Private beach, Kayak, yard games
Big Pine Key condo rentals
Condo in Key Colony Beach
4.81 out of 5 average rating, 109 reviewsBeachside Unit 28 - Private Beach, Pool & Paradise
Condo in Marathon
4.94 out of 5 average rating, 99 reviewsJune Discount! Marina, Pool, Tiki Bar, Waterside!
Condo in Marathon
4.88 out of 5 average rating, 201 reviewsSombrero Beach Tropical Getaway
Condo in Key West
4.93 out of 5 average rating, 135 reviewsBeach Club Ocean Front 2BR Condo
Condo in Key West
4.89 out of 5 average rating, 153 reviewsLarge waterfront 2/2 end unit with boat slip
Condo in Key West
4.86 out of 5 average rating, 133 reviewsA Perfect Getaway
Condo in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
Condo in Key West
4.86 out of 5 average rating, 112 reviewsRooftop Penthouse
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
$50 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 houseboat rentals in Big Pine Key?
Experience the best of Big Pine Key with our houseboat rentals, starting at about $220 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Big Pine Key vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 100 vacation homes with pools in Big Pine Key, available on Airbnb. Make a splash and soak up the sun in style!
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 rv rentals in Big Pine Key have wifi?
Absolutely! We offer over 10 rv rentals with wifi in Big Pine Key. Enjoy a tailored experience with all the comforts you desire.
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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- Rentals with outdoor seating Big Pine Key
- Rentals with a fire pit Big Pine Key
- Cottage rentals Big Pine Key
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- Waterfront rentals Big Pine Key
- Pet-friendly rentals Big Pine Key
- House rentals Big Pine Key
- Rentals with pools Big Pine Key
- Family-friendly rentals Big Pine Key
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- Rentals with beach access Big Pine Key
- Monthly Rentals Big Pine Key
- Rentals with a kayak Big Pine Key
- Rentals with a washer and dryer Big Pine Key
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