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.
The Local House

The Local House

South Beach
CA $1,284
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
Casablanca Miami Beach

Casablanca Miami Beach

North Beach
CA $6,961
per person
Oct 2 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (327 reviews)
Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No beach chair, no wagon and the umbrella covered 1 person. I reached out to the person but never showed up with clean sheets. I had to invest in my stay detergent, sanitizing wipes, trash bags and toilet covers. Let me know forget to say, on my first stay the bottom of my feet was all black from the floors being super dirty. The only good thing of the place was the beach distance.

Reviewed on Jul 23, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
CA $16,329
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Viscay Hotel

Viscay Hotel

South Beach
CA $2,591
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand

Reviewed on Jul 16, 2026

Pantera Rosa

Pantera Rosa

South Beach
CA $1,296
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (74 reviews)
The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.

Reviewed on Jun 26, 2026

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
A steel bridge over turquoise water with a clear sky.

Sands

Though Sands 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.

A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

Long Beach Estates

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

A coastal scene with a pier extending into turquoise waters, a beachfront building, and sailboats in the distance.

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.

A long, rusted bridge over a body of water with a cloudy sky.

Pine Channel Estates

While there might not be top attractions in Pine Channel Estates, you can explore the larger area and discover places like Big Pine Key Flea Market and Coupon Bight Aquatic Preserve.

A coastal scene with a pier extending into the ocean, surrounded by palm trees and greenery.

Eden Pines

While there might not be top attractions in Eden Pines, you can explore the larger area and discover places like Big Pine Key Flea Market and Coupon Bight Aquatic Preserve.

Ready to book your vacation to Big Pine Key?

Choose your dates

Big Pine Key Hotel Deals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL
CA $125
CA $337 total
Sep 1 - Sep 2
includes taxes & fees
Old Wooden Bridge Resort and Marina
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

38801 Overseas Highway Big Pine Key FL
8.8/10 Excellent! (173 reviews)
"Love staying at sunshine key and always rent their cabins. The tiny homes are beautiful and have a great view. The RVs need some upgrading ASAP. The staff is very attentive and accommodating"

Reviewed on Aug 10, 2026

Get rates
Sunshine Key RV Resort & Marina
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

1 Knights Key Boulevard Marathon FL
Fully refundableReserve now, pay when you stay
CA $312
CA $436 total
Aug 12 - Aug 13
includes taxes & fees
Isla Bella Beach Resort & Spa
See all 2,635 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.

Stay near popular Big Pine Key attractions

A beach with a pier extending into the ocean during sunset.

Florida Keys Beaches

8.4/10 (858 reviews)
Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates.
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A beach with clear turquoise water, a sandy shore, palm trees, and a steel bridge over the water.

Bahia Honda State Park

9.4/10 (50 reviews)
You can take time to visit Bahia Honda State Park during your travels to Big Pine Key. While you're in the area, wander around the natural setting.
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A beach with clear turquoise water, a sandy shore, and a long pier extending into the water.
Photo by Sérgio Veludo

Calusa Beach

7.8/10 (9 reviews)
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.
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A clear blue sky, calm sea, and a tree with exposed roots on a sandy beach.

Sandspur Beach

10.0/10 (1 review)
Why not spend a lazy afternoon at Sandspur Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting.
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Key West Visitors Center

8.4/10 (85 reviews)
After visiting Key West Visitors Center, make a plan to see the other sights and activities in Big Pine Key. Amble around this relaxing area's marina, or seek out the fishing spots.
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Big Pine Key Flea Market

8.2/10 (12 reviews)
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.
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National Key Deer Refuge Visitor Center

8.4/10 (50 reviews)
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.
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Coupon Bight Aquatic Preserve

Commune with nature and explore the great outdoors at Coupon Bight Aquatic Preserve during your travels in Big Pine Key. While in this romantic area, you can enjoy the restaurants.
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What to do in Big Pine Key

Florida Keys Nature & History Tour from Key West

Florida Keys Nature & History Tour from Key West

CA $167
per adult
88% of travellers recommend
Florida Keys Nature & History Tour from Key West
Marathon Key FL: Snorkel Trips and Sunset Cruises

Marathon Key FL: Snorkel Trips and Sunset Cruises

CA $97
per adult
Marathon Key FL: Snorkel Trips and Sunset Cruises
Marathon FL Sandbar Cruise & Sightseeing Adventure

Marathon FL Sandbar Cruise & Sightseeing Adventure

CA $160
per adult
100% of travellers recommend
Marathon FL Sandbar Cruise & Sightseeing Adventure
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 $1,284 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.

Explore a world of travel with Expedia

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