How much does a Big Pine Key vacation package cost?

You can grab a vacation package to this destination from $353 on Expedia. But how much your vacation to Big Pine Key costs will depend on factors like the season, length of stay and hotel choice.

What are the cheapest months to go to Big Pine Key?

If you're looking to score a cheap Big Pine Key vacation package, consider visiting in August, September and October. You'll typically find better rates on airfares and hotels during these months — ideal for a budget-friendly break.

How many days is enough for Big Pine Key?

To get the most out of a Big Pine Key vacation, we recommend booking for 3 days. Split your time between visiting Loggerhead Beach , Sandspur Beach and other leading sights, on top of exploring neighborhoods like Long Beach Estates and Punta Brisa. If you've got some time to spare, include a day trip in your Big Pine Key vacation itinerary.

Is it worth booking a vacation package to Big Pine Key?

Big Pine Key has everything you need for an awesome break — fishing, views and walking trails are just the start. Whether you want to check out attractions such as National Key Deer Refuge Visitor Center and Big Pine Key Flea Market , or take the road less traveled, you'll have plenty to see and do on your Big Pine Key vacation.

How to find the best Big Pine Key package deals?

Bagging a cheap Big Pine Key package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most economical Big Pine Key package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.

Is it cheaper to book a Big Pine Key vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Big Pine Key vacation by choosing your favorite airline, accommodation type and car class.

When to book a vacation package to Big Pine Key?

If you're planning an impromptu Big Pine Key trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking ahead.

How to plan a trip to Big Pine Key?

Choose when to go: Check your calendar and get your bags packed. Your favorite time of year and the activities on offer will also help you decide when to escape to Big Pine Key. Figure out your budget: Make sure you have enough money to pay for everything from meals and transportation to experiences and flights. Your hotel will probably be the biggest expense during your trip to Big Pine Key. Use our trip planning tool to discover Big Pine Key: Research every aspect of your trip to Big Pine Key with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings. Decide how long to go for: Now that you know more about Big Pine Key, you can work out the perfect length of your vacation. Pull together a rough plan and give yourself enough time to get through everything on your must-do list. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Big Pine Key vacation package that brings all your bookings together. Book any activities or excursions: Here's the fun part — organizing everything you want to see and do. Explore some of the exciting things to do in Big Pine Key and reserve your tickets in advance to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Big Pine Key vacation packages?

Secure your perfect escape to Big Pine Key with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until your next paycheck — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stay on budget and snap up cheap deals while they last.

Big Pine Key Vacation Packages 2025/2026 from $385

Name: Sunshine Key RV Resort & Marina
Rating: 8.6

Your Big Pine Key Vacation

The easiest way to experience this vibrant city is with a custom-made Big Pine Key vacation package. Base yourself in the neighborhood of Breezeswept Beach Estates, which is great for adventure sports, fishing and watersports or choose someplace else — our packages are all about you. If your trip to Big Pine Key includes some sightseeing, drop by renowned attractions like Bahia Honda State Park, Calusa Beach and Loggerhead Beach. Whatever your travel plans or the size of your budget, organizing a tailored Big Pine Key vacation is a walk in the park with Expedia.

The Latest Big Pine Key vacation packages

Price found within the past 48 hours. Click for updated prices.

President Villa

South Beach

Save 100% on your flight

$353

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,000 reviews)

Hospitable staff, clean, location ideal to walking distance to beach and shopping. Safe place!

Reviewed on Aug 8, 2025

Park Central South Beach

South Beach

$495

per person

Oct 24 - Oct 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (930 reviews)

I appreciated the close location to the beach. We were literally a walk across the street to the beach. Everything was walkable. The staff were attentive & present. Very helpful and friendly & accommodating. The lobby area always was clean smelling. I liked they provided complimentary bikes to ride, beach chairs & bottled water. What I did not like were the little bit of channels available on the tv. The stations they did have did not have service so it did not work. Would also recommend a full length mirror.

Reviewed on Aug 23, 2025

Cavalier Hotel South Beach

South Beach

$426

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,000 reviews)

Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.

Reviewed on Aug 16, 2025

Henrosa Hotel

South Beach

Save 100% on your flight

$386

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (814 reviews)

Good location, very walkable. Front desk staff is very nice.

Reviewed on Aug 8, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,953

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

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Where to stay in Big Pine Key

Find the best Big Pine Key areas and neighborhoods for the activities you enjoy most. Learn more about Big Pine Key

Big Pine Key Hotel Deals

Old Wooden Bridge Resort and Marina

1791 Bogie Drive, Big Pine Key, FL

$222 nightly

$250 total

Sep 7 - Sep 8

Total with taxes and fees

8.6/10 Excellent! (256 reviews)

"River boat houses, pool, kayak rentals."

Reviewed on Aug 14, 2025

Barnacle Resort

1557 Long Beach Dr, Big Pine Key, FL

Fully refundableReserve now, pay when you stay

$274 nightly

$309 total

Aug 26 - Aug 27

Total with taxes and fees

8/10 Very Good! (40 reviews)

"No communication when I couldn’t get into my room. Horrible situation. DO NOT STAY AT THIS PROPERTY!! Total scam."

Reviewed on Jun 29, 2025

Sunshine Key RV Resort & Marina

38801 Overseas Highway, Big Pine Key, FL

8.6/10 Excellent! (156 reviews)

"Perfect"

Reviewed on Aug 18, 2025

Get rates

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do in and around Big Pine Key

Big Pine Key is perfect for outdoor and adventure vacations, offering various activities such as exploring pine campgrounds, enjoying kayak access, and discovering excellent fishing spots. Visitors can unwind at recreational areas, shop at local centers, and immerse themselves in the unique charm of this Florida getaway. Whether you're seeking relaxation or adventure, Big Pine Key has something for everyone to enjoy.

Shopping

The Big Pine Key Flea Market offers a vibrant local scene with a variety of unique gifts and souvenirs. If you're up for a drive, We Cycle Key West and The Kite House, both about 29 miles away, feature great selections for outdoor enthusiasts and kite lovers.

Recreation

Experience luxury at Florida Keys Country Club, just 17 miles from Big Pine Key, offering a serene atmosphere for relaxation. For outdoor enthusiasts, Key West Golf Club, 25 miles away, invites you to enjoy sports amidst beautiful scenery. Embrace culture and entertainment at the Key West Burlesque Theater, 29 miles from your retreat.

Adventure

Pigeon Key offers thrilling water sports, located 13 miles from Big Pine Key, where you can enjoy activities like kayaking and paddleboarding in a vibrant outdoor atmosphere. For more adventure, visit Keys Cable Park, 27 miles away, where you can experience wakeboarding and other exciting water activities.

Nightlife

In Big Pine Key, enjoy a laid-back nightlife at local bars and restaurants offering live music and fresh seafood. Visit the nearby No Name Pub for a fun atmosphere or unwind at the tiki bars along the water, where you can sip cocktails while soaking in the sunset views.

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

Find the best attractions in Big Pine Key

Big Pine Key offers a perfect blend of outdoor adventure and beach relaxation for travelers. Explore beautiful beaches, visit the nearby Pigeon Key, and enjoy the stunning landscapes of the Florida Keys. National and state parks in the area provide excellent opportunities for family-friendly activities, making it an ideal destination for nature lovers and those seeking a fun-filled vacation.

Calusa Beach: Enjoy the sun and sand at Calusa Beach, a serene spot on Big Pine Key. With its laid-back beach vibes, it's perfect for swimming, sunbathing, and picnicking while soaking in the stunning ocean views.
Key West Visitors Center: The Key West Visitors Center offers a gateway to adventure. Engage in family-friendly activities, gather local insights, and embark on exciting outdoor excursions that highlight the area's natural beauty and rich history.
National Key Deer Refuge Visitor Center: Explore the National Key Deer Refuge Visitor Center, where adventure awaits. Discover unique wildlife, including the endangered Key deer, and enjoy outdoor activities that connect you with the region's natural wonders.

Tips to save on your trip to Big Pine Key

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Big Pine Key during the low season (August to October) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.