Big Pine Key Vacation Rentals

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Make Big Pine Key your next getaway

Big Pine Key vacation rentals put you in the best position to savor the Florida Keys’ unique cultures, flavors, and adventures. 

Top Big Pine Key property types

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House rentals

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Popular amenities for Big Pine Key vacation rentals

Popular
Dog-friendly Hot tub Internet
Big Pine Escape
3 Bedroom | 2 Bath | Sleeps 6

Big Pine Escape - Big Pine Key, FL

$227 avg / night
(excludes fees and taxes)
5.0 (4)
Big Pine Key Dreams
2 Bedroom | 2 Bath | Sleeps 6

Big Pine Key Dreams - Big Pine Key, FL

$171 avg / night
(excludes fees and taxes)
4.86 (7)
Octopus Palms
3 Bedroom | 1 Bath | Sleeps 6

Octopus Palms - Big Pine Key, FL

$215 avg / night
(excludes fees and taxes)
Tropical Valhalla
3 Bedroom | 2 Bath | Sleeps 8

Tropical Valhalla - Big Pine Key, FL

$265 avg / night
(excludes fees and taxes)
Sunset Villa
3 Bedroom | 2 Bath | Sleeps 6

Sunset Villa - Big Pine Key, FL

$186 avg / night
(excludes fees and taxes)
4.0 (3)

View 2 more homes

Recent Big Pine Key guest reviews

I rented Big Pine Escape to have extra room for family visiting from up North. Rather than have them crowd my house here in the Key, I found a perfect spot near enough to enjoy their time here with them and private enough for them to enjoy their vacation time on their own. The house and property are perfect for comfort and seclusion, and my family was completely satisfied with their stay. If you’re a Snowbird heading south to visit family or friends who live and work in the Lower or Middle Keys, Big Pine Key offers the ideal combination of proximity, privacy, and peace. Instead of crowding their house or staying somewhere impersonal, this location gives you the space to relax and explore while remaining just a short, easy drive from your loved ones. Big Pine is centrally located in the Lower Keys. You're close enough to drive to Key West for a day trip or head up to Marathon for dinner, making it an excellent hub for activities. Critically, it’s only 30-45 minutes from most local communities (like Marathon, Cudjoe, or Key West), ensuring you can pop over easily for grandkids’ soccer games or family dinners without committing to the congestion of a major town. My family especially enjoyed access to the owner’s e-bike. It’s a short ride to the new community park Pickleball courts, where we would meet regularly throughout their stay. These new courts are a welcome addition to our community.
Katty C. | Nov 2025
What a perfect location. Close enough to stores and amenities, but quiet and secluded for a Keys get away.
Craig W. | Nov 2025
The location was very much a neighborhood and quiet and friendly. We know the owners personally so we enjoyed the time there and they have done an amazing job with the place and the decor. The 2 bonus features are a large hot tub with a curtain cover privacy and the screen in I. Porch down below. Great uses of space! There are cute bars and restaurants nearby so access is perfect for any type of food or drink you may want. The place feels like a total vacation!
Jan and Gail D. | Nov 2025
Big Pine Key vacation rental FAQ

Yes, 5 of our Big Pine Key homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 19 of our Big Pine Key vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Big Pine Key vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Big Pine Key team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Big Pine Key, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

But Big Pine Key house rentals have another huge benefit, too: With vacation rentals of many shapes and sizes available, you’re sure to find a home base that fits your next vacation. 

 

Why do they call it Big Pine Key?

Big Pine Key is named for its slash pine forest, the largest remaining population of the pine in Southern Florida. 

The unique ecosystem of limestone and slash pine provide sanctuary for the famous—and endangered—Key deer. About the size of a medium dog, Key deer can only be found in the Florida Keys. Stay in a Big Pine Key vacation rental, and you might get to see one of these adorable creatures (and have the opportunity to learn more about them at the National Key Deer Refuge Nature Center). 

Is Big Pine Key worth visiting? 

Big Pine Key is absolutely worth visiting. Beyond the 8,500-acre National Key Deer Refuge, Big Pine Key house rentals offer guests oustanding access to some of the country’s best natural scenery. Discover hundreds of species of flora and fauna—including more than 20 endangered and threatened plant and animal species—at nearby wildlife trails on the island. 

Big Pine also features the famous Blue Hole, an abandonded quarry that is now the only freshwater lake in the Florida Keys. It’s now home to lots of wildlife, including alligators, birds, snakes, and green iguanas.

Snorkeling and diving are favorite pastimes around these parts. There are several places that will accommodate day and night dive and snorkel trips for those less-experienced travelers. The 210-foot wreck of Adolphus Busch, Sr. is easily accessible from Big Pine Key, as is the Looe Key coral reef, part of the Florida Keys National Marine Sanctuary. In fact, every year, an underwater music festival is held at the coral reef. Attendees are invited to explore the last living coral reef in the continental United States as they sway and swim to a sub-sea concert. 

Day Trips from Big Pine Key, FL

Just a little more than two dozen miles away lies the island chain of Marathon. With its mangrove and coral reefs, it boasts diverse landscapes and wildlife befitting of a gorgeous Sunshine State destination. 

Fewer than 30 miles away sits the renowned Key West. Characterized by a lively arts culture and tons of outdoor activities, this ecotourist-friendly city will wow you with its beauty and charm.

When Florida is calling your name and you just can't shake that desire for a tropical getaway, give Big Pine Key vacation rentals a try. You'll find yourself leaving with more than just a nice tan: you'll take with you a lifetime of fun-in-the-sun memories.

Discover Big Pine Key

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