Big Pine Key vacation rentals

We found 702 vacation rentals — enter your dates for availability

Discover a selection of 143 homes and other vacation rentals in Big Pine Key that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the amenities you need and want, which might include WiFi and a washer and dryer. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Big Pine Key

Why visit Big Pine Key

  • Outdoor paradise: Big Pine Key is perfect for outdoor enthusiasts, offering activities like hiking, snorkeling, and fishing.
  • Stunning beaches: Relax on picturesque beaches and soak in the sun at locations like Gulf Shores and Myrtle Beach.
  • Unique wildlife: Spot the adorable Key deer, a rare species found only in the Florida Keys.
  • Nearby islands: Explore charming nearby islands, including Pigeon Key and Caribbean Oasis, for unforgettable experiences.
  • Diverse accommodations: Choose from a variety of vacation rentals, from cozy cottages to modern condos, tailored to your needs.

Popular types of accommodation in Big Pine Key

Discover the charm of Big Pine Key with a variety of vacation rentals that cater to every traveler's needs. Whether you're looking for houses, cozy cottages, or modern condos, you'll find the perfect spot to unwind. Enjoy essential amenities and easy access to the stunning Florida Keys. Explore our selection of rentals in Big Pine Key, FL, and make your dream getaway a reality.

  • Houses: The top choice for travelers to Big Pine Key, offering spacious settings perfect for families or groups.
  • Condos: A popular option for those seeking modern amenities and a convenient location near attractions.
  • Cottages: These charming abodes provide a cozy and quaint atmosphere, ideal for a relaxing getaway.
  • Apartments: A versatile option that offers comfort and flexibility for both short and extended stays.
  • Villas: Luxurious and spacious, villas are perfect for those wanting an upscale vacation experience.**

Top attractions in Big Pine Key

Big Pine Key is a paradise for outdoor enthusiasts and beach lovers, offering a range of activities and attractions that cater to families and adventurers alike. Explore the stunning beaches, visit nearby islands, and discover the beauty of national parks. Notable points of interest include Pigeon Key, Gulf Shores, Myrtle Beach, and Caribbean Oasis, all perfect for creating unforgettable memories in this tropical haven.

  • Bahia Honda State Park: A stunning national park famous for its pristine beaches and crystal-clear waters. Visitors can enjoy hiking, snorkeling, and kayaking amidst beautiful scenery and diverse wildlife.
  • Calusa Beach: A tranquil beach known for its soft sand and relaxing atmosphere. Ideal for sunbathing, swimming, and enjoying breathtaking sunsets over the Gulf of Mexico.
  • Key West Visitors Center: The perfect starting point for your adventure, offering information on local attractions, tours, and family-friendly activities to explore the vibrant culture of Key West.

Things to do recommended for couples

Looking for a romantic getaway in Big Pine Key? Enjoy a luxurious day at the Florida Keys Country Club, only 17 miles away. Indulge in fine dining, play a round of golf, and soak in the stunning views together for a memorable couple's experience.

Things to do recommended for families

Families visiting Big Pine Key can explore the beautiful National Key Deer Refuge, where kids can spot the tiny Key deer, and enjoy a day at Bahia Honda State Park, perfect for swimming and picnicking on sandy beaches. Don’t miss the chance to go snorkeling in crystal-clear waters.

Things to do recommended for groups

Groups visiting Big Pine Key can enjoy snorkeling at the nearby Looe Key Reef, embark on a kayak tour through the mangroves, and participate in a sunset picnic at the beautiful Bahia Honda State Park for a memorable outdoor experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Big Pine Key

If you're traveling with a group, family, pets, or planning an extended stay, be sure to set your filters based on your specific needs. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Big Pine Key with a group: Think about how many bedrooms you'll require, as well as any amenities like a complete kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Big Pine Key with young kids: Traveling with young kids can be challenging. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Big Pine Key: For many families, a vacation wouldn’t feel complete without their beloved pets joining the fun. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that both you and your furry friend feel right at home.
  • Planning for a long term stay visiting Big Pine Key: If you're in search of vacation rentals that offer great deals for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can conveniently discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Big Pine Key

Big Pine Key offers an unforgettable vacation experience, combining stunning natural beauty with outdoor adventures. Enjoy the warm, family-friendly atmosphere while exploring the nearby Florida Keys, perfect for romantic getaways or relaxing family trips. Don’t miss the chance to spot the adorable Key deer and unwind at picturesque beaches. With its vibrant community and diverse excursions, Big Pine Key is the ideal spot for creating lasting memories in paradise.

  • Little Torch Key: Located a mere 2 miles from Big Pine Key, Little Torch Key is a charming village that offers a quintessential island experience. With its beautiful beaches and family-friendly atmosphere, it's perfect for outdoor enthusiasts. Visitors can take advantage of the local recreational areas, explore shopping venues, and enjoy nearby shopping mall centers. Notable attractions include pristine beaches and family-oriented spots that promise relaxation and fun in the sun. Whether you're seeking adventure or tranquility, Little Torch Key has something for everyone.
  • Bahia Honda Key: Situated in close proximity to Big Pine Key, Bahia Honda Key is renowned for its stunning natural beauty and outdoor adventures. As an island paradise, it offers an array of activities, from swimming and snorkeling to hiking in the state park. The area's recreational facilities and shopping mall center cater to all your needs. Bahia Honda is home to some of the most picturesque beaches in the Florida Keys and features a national state park that showcases the region's unique flora and fauna. It's an ideal spot for those looking to immerse themselves in nature.
  • Long Beach Estates: Nestled around Big Pine Key, Long Beach Estates is a delightful neighborhood perfect for adventurous travelers. The area boasts excellent recreational facilities and a variety of resorts, making it a great base for relaxation and exploration. Visitors can enjoy nearby shopping centers and indulge in the local culinary scene. With easy access to beautiful beaches and a national state park, Long Beach Estates provides a wonderful blend of adventure and leisure, catering to families and solo travelers alike.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient area for you to plan new trips, keep your travel arrangements on track, and manage your bookings efficiently. Your saved or booked properties are now organized into categories: Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The charming area of Big Pine Key awaits your stay

The island views and other outdoor surroundings create an inviting atmosphere in Big Pine Key. Travelers to this romantic city praise the fishing, kayaking and snorkeling. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Big Pine Key

Are you searching for attractions to see in the city? Venture out of your cozy vacation rental and experience everything that Big Pine Key has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Florida Keys Country Club (17.3 mi / 27.9 km)
  • Blue Hole (2.3 mi / 3.7 km)

Exploring the natural features in Big Pine Key

Whether you're an outdoor enthusiast or just want to take in the scenery, Big Pine Key is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Florida Keys Beaches (13.2 mi / 21.3 km)
  • Calusa Beach (4.8 mi / 7.7 km)
  • Upper Sugarloaf Key (10.9 mi / 17.5 km)
  • Pigeon Key (12.7 mi / 20.4 km)
  • Sugarloaf Beach (13.6 mi / 21.9 km)
  • Vaca Key (14.8 mi / 23.9 km)

Transportation options to and around Big Pine Key

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

Frequently asked questions

What is the best area to stay in Big Pine Key, Florida, United States of America when booking a vacation rental?
When considering a vacation rental in Big Pine Key, Florida, a popular area to stay is around the peaceful neighborhoods that offer a blend of natural beauty and local charm. This region is known for its serene atmosphere, making it an ideal spot for relaxation while still being close to various attractions.

One popular neighborhood is near the National Key Deer Refuge, which not only provides an opportunity to observe the unique Key deer but also offers a variety of walking trails and scenic spots for picnicking. The area is also close to the Big Pine Key Community Park, where visitors can enjoy recreational activities, including basketball courts and playgrounds, great for families.

Another appealing area is close to the waterfront, where you can enjoy stunning views and easy access to the ocean. This location often features vacation rentals with access to kayaking and fishing, allowing you to fully embrace the outdoor lifestyle that the Florida Keys are known for. The nearby Blue Hole, a former limestone quarry turned freshwater lake, is a fantastic spot for birdwatching and offers a tranquil setting for nature lovers.

With a mix of cozy homes and waterfront properties, Big Pine Key has a variety of vacation rentals that cater to different preferences, ensuring you can find the great base for your getaway.
How much does it cost to rent a vacation home in Big Pine Key?
Prices for vacation rentals in Big Pine Key vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Big Pine Key to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Big Pine Key vacation house rentals?
You can find great discounts on house rentals in Big Pine Key on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Big Pine Key?
For renting a beach house in Big Pine Key, travelers should focus on the scenic areas along the Florida Keys' coastline. The area near Big Pine Key's National Key Deer Refuge offers vacation rentals that provide access to beautiful waterfront views and a tranquil environment. Many properties in this region feature amenities such as private docks, outdoor grills, and spacious decks that are great for enjoying sunsets over the water.

Additionally, the nearby Bahia Honda State Park is a fantastic spot for beach lovers, where you can find rentals that are just a short drive away from pristine beaches and excellent snorkeling opportunities. These accommodations often come with outdoor showers, beach gear, and even kayak rentals, allowing guests to fully immerse themselves in the natural beauty of the area.

Travelers can also explore the local dining scene in Big Pine Key, where many rental properties are conveniently located near popular seafood restaurants and shops. For those seeking adventure, the nearby waters offer fishing, boating, and paddleboarding options, making it an ideal destination for both relaxation and outdoor activities.
What is the most popular type of vacation rental accomodation in Big Pine Key?
In Big Pine Key, vacation houses are the most popular type of rental, with approximately 130 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups looking to enjoy a cozy feel. Many vacation houses also offer outdoor spaces, such as decks or patios, great for taking in the beautiful Florida sunsets or enjoying a BBQ after a day of exploring the nearby natural attractions, including the National Key Deer Refuge.

In addition to vacation houses, there are several mobile homes, apartments, and cabins available, each providing a great experience for travelers. Mobile homes often come with amenities that allow for a comfortable stay, while apartments and cabins present cozy options for those seeking a more intimate retreat.
Are there any family house rentals in Big Pine Key?
In Big Pine Key, there are numerous family-friendly rentals available, with around 85 options to choose from. This scenic area offers an array of homes that cater to families, featuring spacious living areas, full kitchens for meal preparation, and outdoor spaces superb for children to play. Many properties also include amenities such as private pools, barbecues, and easy access to the nearby waters for swimming or kayaking.

Visitors can explore attractions like the National Key Deer Refuge, where families can encounter local wildlife and enjoy nature trails. Additionally, the proximity to the stunning beaches and parks makes it an ideal spot for outdoor activities.
Can I rent a vacation home with a pool or hot tub in Big Pine Key?
In Big Pine Key, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 61 options to choose from. This idyllic location in the Florida Keys offers a range of neighborhoods where these properties can be found, such as the peaceful residential areas surrounding the National Key Deer Refuge, which provide a serene environment great for relaxation.

Travelers can expect to find a variety of amenities in these rentals, including private pools, hot tubs, and outdoor spaces ideal for entertaining. Many properties also come with fully equipped kitchens, spacious living areas, and some even offer direct access to the water for boating or fishing enthusiasts. Find your rental in Big Pine Key with a pool or a hot tub.
Can I find long-stay vacation rentals in Big Pine Key?
A long-stay vacation rental in Big Pine Key is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Big Pine Key?
In Big Pine Key, there are numerous pet-friendly house rentals available, with around 86 options to choose from. Many of these vacation homes come equipped with amenities such as private pools, spacious backyards, and fully stocked kitchens, making them ideal for families and pet owners. The area offers a laid-back atmosphere, superb for enjoying the sunny Florida Keys.

Pet-friendly points of interest nearby include the beautiful beaches and nature trails of the Big Pine Key Nature Center, where pets are welcome to join their owners on outdoor adventures. Additionally, the nearby National Key Deer Refuge provides ample opportunities for pet-friendly walks amidst stunning natural surroundings. See all pet-friendly rentals in Big Pine Key.
Are there any remote work vacation rentals in Big Pine Key?
In Big Pine Key, there are numerous options for remote work vacation rentals, with around 129 available throughout the area. This beautiful location in the Florida Keys provides a serene atmosphere, superb for productivity and relaxation. Many properties come equipped with essential amenities for remote workers, such as high-speed Wi-Fi, dedicated desk spaces, and comfortable desk chairs, ensuring a conducive work environment.

Travelers can expect to find a mix of charming homes and cozy cottages, often featuring outdoor spaces where one can unwind after a day of work. Proximity to local attractions, such as the nearby National Key Deer Refuge and the stunning waters of the Florida Keys, allows for opportunities to explore nature and enjoy leisure activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Big Pine Key vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Big Pine Key with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Big Pine Key?
In Big Pine Key, popular vacation rental amenities cater to a variety of traveler needs. Most rentals include a fully equipped kitchen, allowing guests to prepare their meals conveniently. Many properties feature decks or patios where visitors can enjoy the tropical surroundings and fresh air. Onsite parking is also commonly available, making it easy for guests to explore the area by car. Additionally, rentals often come with coffee and tea makers for that morning boost. For those traveling with pets, a number of vacation rentals allow pets, ensuring that furry companions can join the vacation fun.
When is the best time to visit Big Pine Key for a vacation rental?
The best time to visit Big Pine Key for a vacation rental is during September, right at the tail end of the peak season that runs from July to September. This month is particularly appealing for travelers seeking a blend of warm weather and fewer crowds, making it a prime time for outdoor adventures like kayaking in the beautiful waters of the Florida Keys or exploring the unique wildlife at the National Key Deer Refuge.

In September, temperatures typically range from the mid-70s to low 90s Fahrenheit, providing a comfortable backdrop for activities such as snorkeling, fishing, and relaxing on the beach. The weather remains inviting, allowing for memorable days spent basking in the sun or taking scenic boat rides through the surrounding islands.

For those looking for a more budget-friendly option, October marks the beginning of the low season. While this time may bring a quieter atmosphere, it also offers an opportunity to experience the natural beauty of Big Pine Key with fewer tourists around. The fall months can be ideal for those who appreciate a more tranquil vacation, enjoying the serene environment and the chance to see migrating birds.
How early should I book a Big Pine Key vacation rental?
Book your Big Pine Key vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Big Pine Key, Florida, United States of America?
In Big Pine Key, visitors can enjoy the natural beauty of the Florida Keys. One of the main attractions is the National Key Deer Refuge, where travelers can observe the endangered Key deer in their natural habitat. The refuge offers walking trails and opportunities for wildlife viewing, making it a great spot for nature enthusiasts.

Another highlight is the Bahia Honda State Park, known for its stunning beaches and clear waters, superb for swimming, snorkeling, and picnicking. Visitors can also explore the historic Bahia Honda Bridge, which provides scenic views of the surrounding area.

For those interested in local culture, the area features quaint shops and restaurants along the Overseas Highway, where you can savor fresh seafood and other local delicacies.
Can I change or cancel my Big Pine Key home rental booking on Vrbo?
To find Big Pine Key vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Big Pine Key vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas