Big Pine Key Vacations from $480

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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.
Luxuri Suites

Luxuri Suites

South Beach
$480
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
6.8/10 (57 reviews)
Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.

Reviewed on Jul 9, 2026

Casablanca Miami Beach

Casablanca Miami Beach

North Beach
$4,160
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
$9,522
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

Ocean Four
Save 100% on your flight
$574
per person
Sep 18 - Sep 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (2,137 reviews)
Pelican Hotel

Pelican Hotel

South Beach
Save 100% on your flight
$610
per person
Oct 2 - Oct 7
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (490 reviews)
The restaurant staff was amazing. The hotel was run-down, and the check-in staff not the greatest.

Reviewed on Aug 4, 2026

Don't see what you're looking for?
See all available trips from Des Moines to Big Pine Key
View all trips

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.

Find hotels in Sands
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.

Find hotels in Long Beach Estates
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.

Find hotels in Whispering Pines
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.

Find hotels in Pine Channel Estates
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.

Find hotels in Eden Pines

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)
The Florida Keys' beaches showcase a coral island landscape with crystal-clear waters ideal for snorkeling. Relax under swaying palms at Bahia Honda State Park or explore marine life at Fort Zachary Taylor.
See properties
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)
Bahia Honda State Park boasts pristine white sandy beaches and the historic Old Bahia Honda Bridge. Snorkel in turquoise waters or hike to panoramic viewpoints for an unforgettable Keys experience.
See properties
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)
Calusa Beach captivates with pristine white sands and crystal-clear waters perfect for snorkeling in Bahia Honda State Park. Enjoy spectacular views of the historic bridge while relaxing under picnic shelters.
See properties
A clear blue sky, calm sea, and a tree with exposed roots on a sandy beach.

Sandspur Beach

10.0/10 (1 review)
Sandspur Beach's pristine white sands and clear, shallow waters make it the crown jewel of Bahia Honda State Park. Snorkel in turquoise waters or stroll the shoreline in this picturesque Florida Keys setting.
See properties

Key West Visitors Center

8.4/10 (85 reviews)
This welcoming information hub offers expert guidance and local discounts for your Florida Keys adventure. Stop by for personalized recommendations and insider tips to enhance your island experience.
See properties

Big Pine Key Flea Market

8.2/10 (12 reviews)
This seasonal open-air market showcases the Florida Keys' local treasures from crafts to seafood. Browse handmade jewelry, vintage clothing, and fresh produce while enjoying the lively community atmosphere.
See properties

Cook Island

9.2/10 (5 reviews)
This secluded Florida retreat is only accessible by boat or seaplane, offering pristine beaches and Atlantic views. Bring supplies for a day of kayaking, snorkeling, and peaceful exploration away from tourist crowds.
See properties

Coupon Bight Aquatic Preserve

This protected marine sanctuary shelters vibrant seagrass meadows and coral patch reefs teeming with life. Glide through crystal-clear waters by kayak to spot manatees and sea turtles in their natural habitat.
See properties

What to do in Big Pine Key

Sunset Cruise

Sunset Cruise

$89
per adult
100% of travellers recommend
Sunset Cruise
Sandbar Adventure Cruise in the Florida Keys

Sandbar Adventure Cruise in the Florida Keys

$102
per adult
100% of travellers recommend
Sandbar Adventure Cruise in the Florida Keys
Marathon Key FL: Snorkel Trips and Sunset Cruises

Marathon Key FL: Snorkel Trips and Sunset Cruises

$69
per adult
Marathon Key FL: Snorkel Trips and Sunset Cruises
See all activities in Big Pine Key

Big Pine Key Hotel Deals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL
$214 nightly
$241 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (362 reviews)
"Everything was very good, except the air conditioning was very noisy and that made it hard to sleep; the rest was very good."

Reviewed on Aug 3, 2026

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! (172 reviews)
"The price is comparable to staying at a resort, so you expect a very nice RV that is clean and well-maintained. Unfortunately, that was not our experience. The unit had cockroaches, which was extremely disappointing. We contacted the office after our first night, but the manager was unavailable. ..."

Reviewed on Jul 15, 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
$303 nightly
$341 total
Aug 11 - Aug 12
Total with taxes and fees
Isla Bella Beach Resort & Spa
See all 2,643 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.

Find the Best Big Pine Key Vacation Packages

Things to do in and around Big Pine Key

Big Pine Key is ideal for outdoor and adventure vacations, offering activities like kayaking, fishing, and exploring scenic campgrounds. Visitors can enjoy recreational areas and shopping centers while soaking in the natural beauty of this Florida getaway. Key highlights include access to kayak launches and prime fishing spots, making it a perfect destination for those seeking both relaxation and excitement.

Shopping

For a unique shopping experience, visit the Big Pine Key Flea Market, where you can find local crafts and souvenirs. If you're up for a drive, The Kite House and We Cycle Key West, both 29 miles away, offer a variety of gifts and specialty items.

Recreation

Experience luxury at the Florida Keys Country Club, just 17 miles from Big Pine Key, where you can unwind amidst pristine greens. Enjoy outdoor sports and breathtaking views at Key West Golf Club, located 25 miles away. For a cultural twist, catch a show at the Key West Burlesque Theater, 29 miles away.

Adventure

Explore Pigeon Key, a thrilling water sports destination located 13 miles from Big Pine Key, where you can enjoy activities like kayaking and paddleboarding amidst beautiful surroundings. For more adventure, head to Keys Cable Park, 27 miles away, and experience wakeboarding and cable activities in an exhilarating setting.

Nightlife

Big Pine Key's nightlife is laid-back yet inviting, featuring local bars like the No Name Pub, known for its vibrant atmosphere and tasty seafood. For a unique experience, enjoy drinks at the nearby waterfront venues, where live music and stunning sunsets create a perfect evening vibe.

*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 is a perfect destination for outdoor and adventure lovers, offering stunning beaches and beautiful parks. Explore the natural beauty of the Florida Keys by visiting local attractions like Pigeon Key and the pristine beaches of Big Pine Key. Whether you're seeking relaxation by the ocean or thrilling outdoor activities, there’s something for everyone to enjoy in this tropical paradise.

  • Calusa Beach: Enjoy the serene vibes of Calusa Beach, a hidden gem on Big Pine Key. With soft sands and gentle waves, it’s perfect for sunbathing, swimming, or simply relaxing under the sun while soaking in the beautiful surroundings.
  • Key West Visitors Center: Dive into adventure at the Key West Visitors Center, where you can gather information for your family-friendly explorations. The center offers insights into local attractions, outdoor activities, and unique experiences to enhance your visit.
  • National Key Deer Refuge Visitor Center: Embrace the outdoors at the National Key Deer Refuge Visitor Center. This center is dedicated to protecting the endangered Key deer and provides opportunities for family-friendly adventures, including hiking trails and wildlife observation.

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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations
Gay Friendly Vacations
LGBTQ Friendly Vacations
LGBTQ Friendly Vacations
Adventure Vacations
Adventure Vacations
Vacations in Month
Where to go when
Where to go when
Honeymoon Vacations
Honeymoon Vacations
Mountain Vacations
Mountain Vacations
Fishing Vacations
Fishing Vacations
Adults Only Vacations
Adults Only Vacations
Waterpark Vacations
Waterpark Vacations
Scuba Diving Vacations
Scuba Diving Vacations
Yoga Vacations
Yoga Vacations
Cheap Vacations
Cheap Vacations
Solo Vacations
Solo Vacations

Frequently asked questions

How much does a Big Pine Key vacation package cost?
You can grab a vacation package to this destination from $480 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.

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.