Discover a selection of 500 vacation rentals in Big Pine Key, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $172 per night, and houses and cottages are popular options for a stay in Big Pine Key. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Big Pine Key
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Destination guide

Big Pine Key keeps a low profile

Big Pine Key is a genuine treasure among the keys strung so prettily from Florida's southern tip. Most only know it as a place name whistling by, as they drive on through to Key West. But Big Pine Key is the very definition of a laid-back, low-key destination. Those thinking of booking Big Pine Key vacation rentals can look forward to simple pleasures. Tranquil boats trips, sublime snorkeling adventures, and chilled sunset vistas—often with the tiny, rare (and exceptionally cute) Key deer skittering in the background.

Things to do

Big Pine Key attractions both cute and fierce

When you've had your fill of fun in the water, there's plenty on dry land to intrigue since this is one of the larger of the Florida Keys. Many with kids head to the National Key Deer Refuge, where there's a good chance of spotting the dwarf (and just heart-melting) Key deer. The Blue Hole offers a very different sort of adventure. This rare, and overlooked, freshwater lake attracts visitors from far and wide, and reportedly even alligators to its waters.

Weather

Warm winter welcome in Big Pine Key

This being the Florida Keys, there are only 2 temperature settings typically seen here—hot and hotter. Many choose not to stay over during the hottest summer months, when it can be humid and showery, too. In fact, you'll find most people booking their Big Pine Key vacation rentals over the winter months of December through March. Temperatures then are a comfortable 70°F, and the threat of storms quite low. Prices, however, will be high. A good compromise is late spring, when temperatures are warm, but rental rates a little cooler.

Natural features

Big Pine Key bursting with wildlife

Some will rent a Big Pine B&B for sun, some for sea. Most for both. But this is a Key where the stunning wildlife really takes centerstage. We've already met the Key deer, with their own preserve at the National Key Deer Refuge. But there's more to Big Pine Key's wildlife riches. There are seagrass meadows and mangrove tidal creeks that shelter manta rays. And green iguanas are everywhere. The Great White Heron National Wildlife Refuge doesn't just shelter the elegant great white heron, either—the endangered hawksbill turtle breeds here, too.

How to get there

Transportation options to and around Big Pine Key

The nearest airport is in Key West Intl. Airport (EYW), located 26.4 mi (42.6 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Marathon, FL (MTH-Florida Keys Marathon), which is 19.3 mi (31.1 km) away.

What are the top vacation rentals in or near Big Pine Key?

From lavish condos to basic log cabins, Vrbo has properties to match every taste and budget. Pack your bags and check out these top vacation rentals in Big Pine Key:

  • "2 Bedroom Accommodation In Big Pine Key": If you're searching for somewhere in Sands with 2 bedrooms and plenty of style, this escape will tick your boxes. Amenities include a kitchen and a barbecue grill.
  • "Canal Front Pool Home": Located in Whispering Pines, this sought-after getaway has 3 bedrooms and lots of handy amenities. An oven and a nearby marina are among them.

For even more great options, use the search bar at the top of the page to find the perfect Big Pine Key vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Big Pine Key?

We all need some time out from time to time. If you're longing for a couple of carefree mornings lounging around in bed with a cappuccino and a good book, we've got some fabulous weekend getaways in and around Big Pine Key. Check out a few of our favorites:

  • "Kayak Boot Key Harbor, 75ft Canal Home" is around 16 miles east of Big Pine Key and the perfect place to relax and unwind. You'll like the amenities here, including a kitchen and a balcony.
  • "Wow Private Pool, Ocean Front" is another top-rated option. It's located around 18 miles to the east of Big Pine Key and features a washing machine, an iron and ironing board and more.

Can I find studio apartments for rent in and around Big Pine Key?

Studio apartments are a simple yet stylish option, perfectly suited for traveling sweethearts or solo adventurers. Spend your days getting acquainted with your surroundings and your nights relaxing in your cozy hideaway. These vacation rentals in or near Big Pine Key are sure to please:

  • After a day filled with outdoor exploration, enjoy total comfort and privacy at "Waterfront Luxury Living Inside And Out". A kitchen and tennis are among the amenities on offer here.
  • "Condo In Old Town Key West's Truman Annex" is another top stay, offering all you need for a heavenly Big Pine Key adventure. Some amenities here include a porch and an outdoor pool.

Can I find short term rentals in or near Big Pine Key?

Whether you're seeking a cozy apartment for you and a pal or a house with enough room for the family, there's no shortage of short-term rentals in and around Big Pine Key. These retreats make a comfortable base for a whirlwind visit:

  • Within close reach of central Big Pine Key, "Coconut Sunsets And Open Water Views" welcomes short-term guests. When you're not chilling out in your comfortable digs, get out and explore the area's best sights.
  • Alternatively, spend a couple of relaxing nights at "Cloud 9 ~ It's Heaven On Earth In This 3b". This comfy, centrally located property makes exploring the sights easy.

What are the best romantic weekend getaways in or near Big Pine Key?

Whether spent in a cabin, a cottage or a treehouse, a romantic weekend getaway is an excellent way to spice up your relationship. Whisk your partner away for a couple of leisurely days at one of these top escapes in or near Big Pine Key:

  • Sneak away on Friday afternoon for a couple of passionate nights at "Sombrero Beach Home On Canal With Private Dock And Heated Pool". Roughly 16 miles from Big Pine Key, this place comes with lots of nice touches, including a swimming pool and a restaurant dining guide.
  • Another place where you can spend a few dreamy days together is "Key West Oasis, Seperate Cottage". Located 30 miles from Big Pine Key, beauty services and a nearby marina add to the ambiance here.

Are there mansions for rent in or near Big Pine Key?

Nothing says "Best. Vacation. Evvv-er." like staying in a mansion. Spoil your loved ones with a memorable escape at one of these mansions for rent in or near Big Pine Key:

  • Approximately 30 miles to the west of Big Pine Key is "Captiva" ~ , Azul Historic Mansion Suite With Community Pool". As well as its grand design and classy interiors, you'll be impressed by its top-notch amenities, such as a swimming pool and concierge services.
  • Another popular option is "Cortez" ~ , Poolview Suite In Azul Mansion". Approximately 30 miles to the west of Big Pine Key, this swish vacation rental gives you a taste of high-class living and comes with a swimming pool, concierge services and more.

What are the best large group vacation rentals in or near Big Pine Key?

Big groups mean gigantic fun. They also mean finding a place that'll easily fit your entire crew. Browse our large group vacation rentals in or around Big Pine Key and spend time with your favorite people under the one roof:

  • You'll have enough space to sprawl out at "New Photos: Drive To Your Getaway". Around 30 miles west of Big Pine Key, this welcoming retreat has 5 bedrooms accommodating up to 12 guests. Top amenities include a swimming pool and a garden.
  • Invite as many as 14 of your favorite folks to "Spectacular Waterfront Estate" and fill its spaces with love and laughter. This popular option has 6 bedrooms and is around 16 miles to the east of central Big Pine Key. It's packed with features to keep your group happy and comfortable, including a water park and a swimming pool.

What are the best houses for rent with a pool in or near Big Pine Key?

Nothing screams fun and frivolity like a pool does. Dig out your inflatable doughnut and check out these houses in or near Big Pine Key that feature this vacation necessity:

  • Round up your crew and enjoy a memorable stay at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". There's plenty to love about this retreat apart from its pool, such as a kitchen and a garden.
  • Spend leisurely days splashing about or finding some peaceful moments beside the water at "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach". This vacation rental is another sought-after option and comes with a fenced pool, free toiletries and more.

Big Pine Key has a tropical savanna climate, with average summertime temperatures fluctuating between 80 ºF and 85 ºF. But there's no need to wait until summertime to visit. Check out the search bar at the top of the page and adjust the filters to find the ideal Big Pine Key vacation rental and organize your getaway for any time of year.

What are the best large family vacation rentals in or near Big Pine Key?

Every family get-together should be memorable. Whether you're organizing a fun escape with the kids or a reunion with the extended family, these large family vacation rentals in or near Big Pine Key offer a comfy home away from home with plenty of space for everyone:

  • Sleeping up to 7 guests in 3 bedrooms, "Cloud 9 ~ It's Heaven On Earth In This 3b" is the perfect place to vacation with the family. This popular getaway is 30 miles to the west of Big Pine Key and has amenities such as nearby ecotour services and a fenced yard.
  • Another top choice is "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach". This vacation rental is 25 miles west of Big Pine Key and features towels, a stair gate and more. With 3 bedrooms accommodating up to 8 people, don't worry about leaving anyone off your invitation list.

When you're ready to step outside your front door, there are plenty of family-friendly attractions in the area to keep everyone happy. Dolphin Research Center, The Turtle Hospital and Great White Heron National Wildlife Refuge should be at the top of your agenda.

Can I find family cabin rentals in or near Big Pine Key?

Escape from everyday life and treat your loved ones to a vacation of a different kind. Stay in one of these family cabins in or near Big Pine Key and get the camping experience — but with all the comforts of home!

  • "Cabin - Sand Is The New Snow - New 4bedroom W" - This popular escape offers free toiletries and coffee and tea making facilities and is around 16 miles east of the center of Big Pine Key.
  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - Another superb choice, this rental comes with cable/satellite TV services, a kitchen and more. You'll find it around 30 miles to the west of Big Pine Key.

For more options, use the search bar at the top of the page and adjust the filters to find the Big Pine Key vacation rental that's perfect for your needs.