Big Pine Key Vacations from $495

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Mondrian South Beach

Mondrian South Beach

4.5 out of 5
South Beach
Save 100% on your flight
per person
Jun 2 - Jun 8
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (2,028 reviews)
I think its time the rooms get renovated, had a 2br suite basic rooms looked better

Reviewed on Apr 29, 2025

Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jun 2 - Jun 8
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,387 reviews)
Overall, the experience was good. Hotel is very good. Couple things that we were not happy about. We chose resort view room but it wasn’t resort view at all, there was no view at all. It was rough roof view. My husband even asked for a better room, they said it’s already an upgraded room but then where’s the view. Also, the shower faucet was so tight that we initially thought it’s stuck and called maintenance.

Reviewed on Apr 29, 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 2 - Jul 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 8
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,740 reviews)
The staff really went above and beyond to be at service. Upon arrival, Juan was amazing accommodating us and really being very personable. At the beach, the guys were friendly and attentive. John Ray and Mark went above and beyond to find our desire spots and ensuring we had al we needed. The staff really made the place !! The poolside bar is another plus!! The food is pretty good! We will definitely go back !!

Reviewed on Apr 28, 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jun 2 - Jun 8
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (5,944 reviews)
Beautiful property, fantastic location and friendly staff.. Did not like the unexpected $60.00/day mandatory fee and lack of amenities those fees provided.

Reviewed on Apr 29, 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
Default Image

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

Find the Best Big Pine Key Vacation Packages

Big Pine Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Population
4,300
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Bahia Honda State Park, Calusa Beach and Loggerhead Beach

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
2.5 out of 5
1791 Bogie Drive, Big Pine Key, FL
Fully refundableReserve now, pay when you stay
The price is $256 per night from May 1 to May 2
$256
includes taxes & fees
$239 per night
May 1 - May 2
8.4/10 Very Good! (222 reviews)
"The only thing i didn't like was my short time there! I wish i would've booked more nights, this place is incredible. Great location, beautiful scenery, friendly helpful staff"

Reviewed on Apr 28, 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
"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 $301 per night from May 7 to May 8
$301
includes taxes & fees
$268 per night
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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Big Pine Key vacation package cost?
You can grab a vacation package to this destination from $495 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

Discover the most popular places to visit in Big Pine Key

Bahia Honda State Park, Beach at the Campground, view to the new Bridge. If you like to get a spot here for your RV, you have to book up to 8 months in advance.

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

Key West Visitors Center

4/5(74 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.

Key West Visitors Center

National Key Deer Refuge Visitor Center

4/5(21 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.

National Key Deer Refuge Visitor Center

What to do in Big Pine Key

Miami: Party Boat Sandbar Island & Toys Bayside Marketplace

Miami: Party Boat Sandbar Island & Toys

$80
per adult
100% of travellers recommend
Miami: Party Boat Sandbar Island & Toys
Experience the Marathon area marine life on your very own private tour

3 Hour Private Snorkeling in Marathon Florida

$720
per traveler
3 Hour Private Snorkeling in Marathon Florida
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

$667
per traveler
Marathon Backcountry Fishing Charter
See all activities in Big Pine Key

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.