Big Pine Key holiday lettings

We found 704 holiday rentals — enter your dates for availability

Discover a selection of 148 homes and other holiday rentals in Big Pine Key that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include parking and a fireplace. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Why visit Big Pine Key

  • Stunning beaches: Enjoy the pristine beaches and crystal-clear waters, perfect for sunbathing and swimming.
  • Outdoor adventures: Engage in various outdoor activities, including hiking, kayaking, and fishing in the beautiful landscapes.
  • Natural beauty: Explore the picturesque islands and the unique ecosystem of the Lower Keys.
  • Family-friendly atmosphere: Experience a welcoming environment ideal for families and couples seeking relaxation and fun.
  • Charming holiday rentals: Choose from a range of delightful vacation homes and cottages for a comfortable stay.

Popular types of accommodation in Big Pine Key

Discover the charm of Big Pine Key with our selection of holiday rentals, including houses, condos, and cosy cottages. Whether you're seeking a serene getaway or an adventure-filled escape, our Big Pine Key vacation rentals cater to all needs. Enjoy the beauty of this unique destination while benefiting from transparency and savings on your stay. Explore your options in Big Pine Key today!

  • Houses: The most sought-after option for a stay in Big Pine Key, offering ample space and privacy for families or groups.
  • Condos: A popular choice for those seeking a blend of comfort and convenience, often featuring shared amenities.
  • Cottages: Charming and cosy, these quaint retreats provide a delightful escape close to nature.
  • Apartments: Ideal for solo travellers or couples, offering a self-catering experience in a compact setting.
  • Villas: Luxurious and spacious, these properties are perfect for indulgent getaways with stunning views.**

Top attractions in Big Pine Key

Big Pine Key is an ideal destination for those seeking outdoor adventures and beach experiences. With its stunning beaches, picturesque islands, and nearby national parks, there are plenty of attractions to explore. Whether you're visiting with family or friends, you'll find a variety of activities that cater to your love for the great outdoors and provide memorable experiences in this beautiful part of Florida.

  • Bahia Honda State Park: This stunning state park offers a unique blend of adventure and natural beauty. With pristine beaches, crystal-clear waters, and lush landscapes, it’s perfect for hiking, swimming, and picnicking while soaking in the scenic vibes.
  • Calusa Beach: Renowned for its tranquil atmosphere, Calusa Beach is ideal for sunbathing and swimming. The soft sands and gentle waves provide a peaceful escape, perfect for unwinding and enjoying the coastal charm.
  • Key West Visitors Center: A hub for outdoor enthusiasts and families, this centre offers information on local attractions and activities. Engage in adventure tours or explore the area's rich history before setting off on your explorations.

Things to do recommended for couples

For a romantic getaway in Big Pine Key, consider thrilling water sports at Pigeon Key, just 8.1km away, or indulge in luxury at the Florida Keys Country Club, located 10.6km from your stay. Both offer unforgettable experiences for couples looking to create lasting memories.

Things to do recommended for families

Families visiting Big Pine Key can explore the stunning beaches of Bahia Honda State Park, perfect for swimming and picnicking. Additionally, the National Key Deer Refuge offers a chance to see the adorable Key deer in their natural habitat, providing a memorable experience for all ages.

Things to do recommended for groups

Explore the vibrant Big Pine Key Flea Market, where you can browse local crafts and enjoy the bustling atmosphere. It's the perfect spot for group activities, soaking in the community vibes while discovering unique treasures.

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

If you're travelling with a group, as a family, bringing your pets, or seeking longer stays, be sure to apply the appropriate filters according to your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Big Pine Key with a group: Think about how many bedrooms you'll require, as well as amenities like a fully-equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Big Pine Key with young kids: Travelling with young children can present some challenges. It's important to prioritise 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, a family holiday isn’t truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Big Pine Key: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding amenities such as a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay in and around Big Pine Key

Big Pine Key offers a delightful mix of natural beauty and outdoor adventures, making it an ideal destination for families and couples alike. Explore the stunning landscapes of the Lower Keys, where you can enjoy relaxing beach vibes and friendly locals. With its unique atmosphere and great location, your vacation here promises unforgettable excursions and memorable experiences in a tranquil island setting.

  • Little Torch Key: Nestled just 1.2km from Big Pine Key, Little Torch Key is a charming village known for its stunning natural beauty and laid-back atmosphere. This island destination is perfect for families seeking outdoor adventures. Visitors can enjoy a variety of recreational activities, including water sports at the beach and leisurely strolls through local shopping areas. The inviting family beach offers a safe and enjoyable spot for children to play, making it an ideal destination for a family day out.
  • Bahia Honda Key: Located in close proximity to Big Pine Key, Bahia Honda Key is an idyllic island retreat renowned for its breathtaking beaches and adventurous spirit. This area attracts outdoor enthusiasts eager to explore its scenic landscapes, including a national state park that showcases the region's rich biodiversity. The local shopping mall centre and recreational areas provide ample opportunities for relaxation and leisure, while the family beach offers a perfect spot for sunbathing and swimming, making it a favourite among nature lovers.
  • Long Beach Estates: Situated around Big Pine Key, Long Beach Estates is a delightful neighbourhood that offers a blend of outdoor excitement and serene beach experiences. Visitors are drawn to its picturesque beaches and the nearby national state park, where exploration and adventure await. This area features various recreational facilities, including resorts and a golf course, catering to both thrill-seekers and those looking to unwind. It's an excellent choice for tourists wanting to experience the best of Florida's coastal charm.

Booking with Vrbo is a breeze

Are you hoping to save some money on your next getaway? We recommend being flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo accommodation that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform to help you plan new trips, continue from where you last paused, or manage your existing arrangements. You can easily view the properties you've saved or booked, which are organised into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/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. Travellers to this romantic city praise the fishing, kayaking and snorkelling. Whether you're planning a family holiday, romantic stay or trip with friends, holiday 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 looking for top things to see and do in the city? Venture out of your holiday home and experience everything that makes Big Pine Key a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for exciting outdoor activities or just want to spend some time taking in the scenery, Big Pine Key is a great place to get out in nature. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Calusa Beach (4.8 mi / 7.7 km)
  • Pigeon Key (12.7 mi / 20.4 km)
  • Florida Keys Beaches (13.2 mi / 21.3 km)
  • Sugarloaf Beach (13.6 mi / 21.9 km)
  • Vaca Key (14.8 mi / 23.9 km)
  • Sombrero Beach (16.9 mi / 27.2 km)

Transport 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 centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Key West, FL (EYW-Key West Intl.), which is 26.4 mi (42.6 km) away.

Frequently asked questions

What is the best area to stay in Big Pine Key when booking a holiday rental?
When considering a holiday rental in Big Pine Key, the area surrounding the National Key Deer Refuge is an excellent choice. This neighbourhood offers a tranquil atmosphere, ideal for those looking to unwind while being close to nature. The refuge itself is a significant attraction, home to the endangered Key deer, which can often be spotted roaming freely. Additionally, the nearby Bahia Honda State Park is renowned for its stunning beaches and crystal-clear waters, superb for swimming, snorkelling, and sunbathing.

In terms of properties, Big Pine Key boasts a variety of holiday rentals, ranging from charming cottages to more spacious waterfront homes, suiting different preferences and group sizes.
How much does it cost to rent a holiday home in Big Pine Key?
Prices for holiday 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 holiday 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, the area around the Atlantic Ocean offers a variety of options that cater to travellers looking for a serene seaside getaway. The properties along the southern shoreline, particularly near the Big Pine Key Nature Centre, provide easy access to the beach and stunning views of the water. Many of these rentals come equipped with amenities such as private docks for boats, outdoor decks for sunbathing, and well-appointed kitchens that make self-catering a breeze after a day spent exploring the local scenery.

In addition, homes closer to No Name Key, just across the bridge, often feature spacious yards, barbecuing facilities, and direct access to water activities like kayaking and paddleboarding. This area is particularly attractive for those seeking a tranquil environment, with some properties offering features such as hammocks and outdoor showers to rinse off after a day in the sun.

For travellers interested in wildlife, the nearby National Key Deer Refuge provides opportunities for nature walks and spotting the unique Key deer. Rentals in this vicinity often reflect the laid-back lifestyle of the Keys, with amenities that promote relaxation, such as hot tubs and community pools.
What is the most popular type of holiday rental accomodation in Big Pine Key?
In Big Pine Key, holiday houses are the predominant type of holiday rental, with around 520 available throughout the area. These properties typically provide spacious rooms, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or decks, which are superb for enjoying the balmy Floridian climate. Many of these homes are located near the waterfront, offering easy access to activities like fishing and boating.

Additionally, there are about 16 apartments and 16 mobile homes scattered across the island, which serve as more compact options for travellers. These units usually come with essential amenities, including kitchen facilities and comfortable living areas. For those seeking a great experience, several cabins and villas are also available, providing a more secluded and picturesque setting for relaxation.
Are there any family house rentals in Big Pine Key?
In Big Pine Key, families will be pleased to find a substantial selection of around 85 holiday rentals suitable for their needs. The area is celebrated for its stunning natural surroundings and proximity to outdoor activities, making it an excellent choice for family getaways. Many of these homes offer spacious living arrangements, fully equipped kitchens for preparing family meals, and outdoor spaces superb for kids to play.

Visitors can also enjoy amenities such as private pools, which provide a fantastic way to relax after a day of exploring, as well as barbecue facilities for enjoyable family cookouts.

The locale is just a short distance from the beautiful beaches of the Florida Keys, where families can partake in swimming, snorkelling, or simply soaking up the sun. Additionally, nearby attractions like the National Key Deer Refuge offer opportunities for nature walks and wildlife spotting, ensuring that there are plenty of activities to keep the entire family entertained during their stay.
Can I rent a holiday home with a pool or hot tub in Big Pine Key?
In Big Pine Key, there are plenty of holiday homes available for rent that feature pools or hot tubs, with around 61 options to choose from. This idyllic location in the Florida Keys offers a selection of properties, including charming waterfront cottages and spacious family homes. Many rentals include private pools, hot tubs, and outdoor patios, making them great for relaxation after a day of exploring the beautiful surroundings.

Amenities often found in these rentals include fully equipped kitchens, laundry facilities, and comfortable living areas, ideal for families or groups. The proximity to the ocean allows for easy access to water activities such as snorkeling and fishing, enhancing the overall holiday experience.
Can I find long-stay holiday rentals in Big Pine Key?
A long-stay holiday rental in Big Pine Key is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Big Pine Key?
In Big Pine Key, there are numerous pet-friendly house rentals available, with a total of 86 options to choose from. The area is known for its stunning natural beauty and relaxed atmosphere, making it a great destination for travellers with pets. Many of these holiday rentals come equipped with amenities such as private pools, outdoor patios, and fully equipped kitchens, allowing for a comfortable and enjoyable stay.

Big Pine Key is also close to various pet-friendly points of interest, including the nearby National Key Deer Refuge, where visitors can explore beautiful trails and enjoy the local wildlife. The tranquil beaches in the area provide additional opportunities for pets to enjoy the outdoors, with some rentals offering easy access to sandy shores.
Are there any remote work holiday rentals in Big Pine Key?
In Big Pine Key, there are numerous remote work-friendly holiday rentals available, with around 516 options for travellers to choose from. This picturesque area in the Florida Keys offers a tranquil environment superb for those who wish to combine work and leisure. Many properties come equipped with essential amenities such as high-speed Wi-Fi, enabling guests to work comfortably from their accommodation.

You can expect to find a variety of properties, including waterfront cottages and spacious family homes, often featuring outdoor spaces like decks or patios where you can enjoy the stunning views. The proximity to local attractions, such as the nearby National Key Deer Refuge, provides opportunities for relaxation and exploration during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Big Pine Key holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Big Pine Key with parking available—perfect for families or travellers 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 rental amenities include fully equipped kitchens, allowing guests to prepare meals at their convenience. Many properties also feature outdoor decks or patios, superb for enjoying the warm Florida climate and stunning sunsets. Onsite parking is commonly available, making it easy for visitors to bring their vehicles. For those who enjoy a warm beverage, rentals often come with coffee and tea makers. Additionally, many accommodations are pet-friendly, welcoming travellers who wish to bring their furry companions along for the adventure.
When is the best time to visit Big Pine Key for a holiday rental?
The best time to visit Big Pine Key for a holiday rental is during September, just after the peak season that runs from July to September. This month offers a wonderful balance of warm weather and fewer crowds, making it ideal for those seeking both relaxation and adventure. With average temperatures around 24 to 30 degrees Celsius, visitors can comfortably enjoy outdoor activities such as kayaking through the mangroves or snorkelling in the vibrant coral reefs nearby.

September presents an excellent opportunity for nature enthusiasts to explore the beautiful surroundings of the Florida Keys. The weather remains pleasantly warm, encouraging sightseeing at local attractions like the National Key Deer Refuge, where you might spot the rare Key deer in their natural habitat.

If you're looking for a more budget-friendly option, consider visiting in October. While this is technically the low season, it still offers lovely weather and a chance to experience the area's natural beauty with significantly fewer tourists. You can enjoy tranquil beaches and explore the local culture without the hustle and bustle typical of peak travel times.
How early should I book a Big Pine Key holiday rental?
Book your Big Pine Key holiday 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 holiday 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?
In Big Pine Key, visitors can enjoy the natural beauty and unique attractions of the Florida Keys. One of the main highlights is the National Key Deer Refuge, where travellers can spot the endangered Key deer in their natural habitat along scenic trails. The area is also known for its excellent opportunities for outdoor activities, such as kayaking and fishing, particularly around the crystal-clear waters of the nearby Florida Bay.

For those interested in marine life, the Looe Key National Marine Sanctuary offers stunning coral reefs and vibrant underwater ecosystems, making it a popular spot for snorkelling and diving. The picturesque beaches, such as those at Bahia Honda State Park, provide a ideal setting for sunbathing, swimming, and picnicking.

Additionally, Big Pine Key offers access to local shops and seafood restaurants, giving visitors a taste of the island's culture and cuisine.
Can I change or cancel my Big Pine Key home rental booking on Vrbo?
To find Big Pine Key holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

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