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.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
The property was quaint and had a lot of character. Staff was nice enough and location was walking distance to most things.

Reviewed on Aug. 7, 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
Oct 25 - Nov 1
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
per person
Oct 25 - Oct 31
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
Rooms were very clean. Lots of food options around and within the hotel.

Reviewed on Aug. 7, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (911 reviews)
great & friendly staff!!

Reviewed on Aug. 8, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
The Ocean view is the best. To be able to hear the ocean while sitting on the balcony watching the stars and ocean vessels is heaven! You must experience the Spa deep body massage! I love this resort! It’s a very romanic atmosphere.

Reviewed on Aug. 9, 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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Whispering Pines

Though Whispering Pines might not have many top sights, you can venture to the surrounding area to see attractions like Big Pine Key Flea Market and Calusa Beach.

Find hotels in Whispering Pines

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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
8.6/10 Excellent! (254 reviews)
"Everything was good except the bathroom had a bath smell all the time and the boat ramp is broken . I"

Reviewed on Jul. 25, 2025

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Old Wooden Bridge Resort and 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 $334 per night from Aug 13 to Aug 14
CA $334
CA $411 total
Aug 13 - Aug 14
includes taxes & fees
8/10 Very Good! (39 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

Barnacle Resort
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! (154 reviews)
"Amazing for families, friends, and couples. A place to return."

Reviewed on Jul. 25, 2025

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Sunshine Key RV Resort & Marina
See all 2,584 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

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 $149
per adult
88% of travellers recommend
Florida Keys Nature & History Tour from Key West
Experience the Marathon area marine life on your very own private tour

3 Hour Private Snorkeling in Marathon Florida

CA $983
per traveller
3 Hour Private Snorkeling in Marathon Florida
See all activities in Big Pine Key

Frequently asked questions

How much does a Big Pine Key vacation package cost?
Offering excellent value package deals from CA $578 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.