Big Pine Key Vacation Packages

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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.

Top Big Pine Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
May-Dee Suites

May-Dee Suites

2.5 out of 5
Hollywood Hills
Save 100% on your flight
per person
Jun. 1 - Jun. 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.4/10 Exceptional! (1,349 reviews)
This is a hidden jewel among the many overrated and over priced hotels/motels nearby. It was very clean and the staff are remarkable.

Reviewed on Apr. 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Jul. 14 - Jul. 18
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Amara Cay Resort

Amara Cay Resort

4 out of 5
Matecumbe
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,216 reviews)
Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down.

Reviewed on Apr. 30, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
7.8/10 Good! (1,006 reviews)
It was a great family resort

Reviewed on Apr. 23, 2025

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (292 reviews)
The pool was nice, the condo was very basic but was fine. Until the pest control came to spray for roaches. We did not see any roaches during our stay but that did worry us for the rest of our stay. The building is aged but is in a good location.

Reviewed on Mar. 17, 2025

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
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Long Beach Estates

While visiting Long Beach Estates, you might make a stop by sights like Florida Keys Beaches and Coupon Bight Aquatic Preserve.

Find hotels in Long Beach Estates

Ready to book your vacation to Big Pine Key?

 

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Big Pine Key Hotel Deals

Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and Marina
2.5 out of 5
1791 Bogie Drive, Big Pine Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from May 1 to May 2
CA $192
CA $355 total
includes taxes & fees
May 1 - May 2
8.4/10 Very Good! (218 reviews)
Our family loved our stay!
"We were very happy with our stay on the hammerhead houseboat. It was just the right size for our family of four and our big dog. The fishing was awesome. We saw amazing sea life from the bridge! And the convenient location to town was ideal. The staff was lovely. There was a pretty extreme smell ..."

Reviewed on Apr. 26, 2025

Old Wooden Bridge Resort and Marina
Sunshine Key RV Resort & Marina
Sunshine Key RV Resort & Marina
2 out of 5
38801 Overseas Highway, Big Pine Key, FL
8.6/10 Excellent! (147 reviews)
"The staff is very informative, pleasant and helpful. The place is super clean. The view is stunning. You can walk around the place and there are also activities. We were a couple and a 10-year-old girl and we really enjoyed it. Thank you very much for a great vacation."

Reviewed on Apr. 26, 2025

Get rates
Sunshine Key RV Resort & Marina
Barnacle Resort
Barnacle Resort
3 out of 5
1557 Long Beach Dr, Big Pine Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $340 per night from May 7 to May 8
CA $340
CA $417 total
includes taxes & fees
May 7 - May 8
8.2/10 Very Good! (34 reviews)
"The staff was great! But the gem of the property is the seclusion with the amazing view of the ocean…Absolutely stunning! Loved it…Would stay there again!"

Reviewed on Apr. 25, 2025

Barnacle Resort
See all 2,535 properties in Big Pine Key
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Big Pine Key vacation package cost?
Offering excellent value package deals from CA $427 on Expedia, you’ll be thrilled with how little a vacation to Big Pine Key costs! Expedia’s packages make travel planning easier and save you more.
What are the cheapest months to go to Big Pine Key?
August, September and October are great times to search for cheap Big Pine Key vacation packages. Choosing to travel in quieter months means you can generally find lower prices on hotels and flights.
How many days is enough for Big Pine Key?
We’d suggest booking a Big Pine Key vacation for at least 3 days. This will give you enough time to visit major attractions including Calusa Beach and Loggerhead Beach, as well as check out neighbourhoods like Punta Brisa and Long Beach Estates. You might even be able to fit in a day trip outside of Big Pine Key.
Is it worth booking a vacation package to Big Pine Key?
Well known for its fishing, watersports and walking trails, a Big Pine Key vacation is a hit with all kinds of travellers. Be sure to visit key sights like No Name Key and National Key Deer Refuge Visitor Centre, and consider renting some wheels for day trips to experience even more.
How to find the best Big Pine Key package deals?
Use Expedia’s handy filters to find some tempting Big Pine Key package deals. When you start your search, just set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your trip for midweek, or search for Big Pine Key package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it’s usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Big Pine Key vacation as a package?
You can enjoy significant savings on your Big Pine Key getaway by booking a tailored vacation package. Check the “Package” heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Big Pine Key?
Enjoy incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Big Pine Key trip.
How to plan a trip to Big Pine Key?

  1. Pick your dates: The things you plan to do in Big Pine Key and your favourite season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to activities and flights. Your hotel will probably be the biggest expense during your trip to Big Pine Key.
  3. Set the duration of your trip: Start by listing all the activities and sights you’d like to experience in Big Pine Key. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that’s left is to pick a Big Pine Key vacation package that brings all your bookings together.

Discover the most popular places to visit in Big Pine Key

Calusa Beach

Calusa Beach

Why not spend a lazy afternoon at Calusa Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting.

Calusa Beach

National Key Deer Refuge Visitor Center

4/5(1 review)

National Key Deer Refuge Visitor Center is just one of the places to see in Big Pine Key, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the beaches.

National Key Deer Refuge Visitor Center

Big Pine Key Flea Market

You can find the perfect gifts to bring home at Big Pine Key Flea Market during your stay in Big Pine Key. Stroll along the marina or discover the sunrises in this relaxing area.

Big Pine Key Flea Market

What to do in Big Pine Key

Florida Keys Nature & History Tour from Key West

Florida Keys Nature & History Tour from Key West

CA $151
per adult
88% of travellers recommend
Florida Keys Nature & History Tour from Key West
Photograph endangered Key Deer

Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

CA $206
per adult
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
Miami: Party Boat Sandbar Island & Toys Bayside Marketplace

Miami: Party Boat Sandbar Island & Toys

CA $111
per adult
100% of travellers recommend
Miami: Party Boat Sandbar Island & Toys
See all activities in Big Pine Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.