Big Pine Key Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 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

Top Flight + Hotel Deals in Big Pine Key

Price found within the past 48 hours. Click for updated prices.
Hilton Cabana Miami Beach Resort

Hilton Cabana Miami Beach Resort

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (292 reviews)
The hotel has potential, but cleanliness definitely needs improvement. Our bathroom had hair stuck to the ceiling of the shower and visible mold in some areas, which was off-putting. Additionally, the parking fees are excessive. Hilton charged $57 + tax for parking, while a lot just two minutes away on foot offered the same service for only $30. For guests already paying a premium to stay here, the parking costs feel unjustified. I’d strongly recommend lowering the price to be more competitive with the surrounding area.

Reviewed on 30 Jul 2025

The Gabriel Miami South Beach, Curio Collection by Hilton

The Gabriel Miami South Beach, Curio Collection by Hilton

4 out of 5
South Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!

Reviewed on 31 Jul 2025

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,786 reviews)
Quiet ,clean property. Nice stay

Reviewed on 31 Jul 2025

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,099 reviews)
Everything was good however same breakfast choices everyday.

Reviewed on 20 Jul 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
They charge a parking fee of 72 dlrs per day plu some additional hotel fees and taxes..so even though you paid your bill theough expedia you still have to pay money ehen checking out. Also pool hours are ridiculous...kid pool closes at 6:30 and i got there at 6 and they eere already closing, next day i got there at 5:45 and they were closed too! So my toddler did not enhoy the slide...they do not have a set time and thaeybtake you out. Crazy! We got this hotel because of the pool

Reviewed on 1 Aug 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

Sands

Though Sands may 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

Top hotels in Big Pine Key

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

Reviewed on 25 Jul 2025

Get rates
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 €248 per night from 26 Aug to 27 Aug
€248
26 Aug - 27 Aug
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 29 Jun 2025

Barnacle Resort
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Big Pine Key
The price is €636 per night from 18 Aug to 19 Aug
€636
18 Aug - 19 Aug
includes taxes & fees
Charming 3-bedroom house in Big Pine Key near Beach and Key West
See all 2,570 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.

Popular places to visit

Big Pine Key Flea Market

You can enjoy retail therapy 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

€94
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

€145
per adult
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

€68
per adult
Guided Clear Kayak Eco-Tour Near Key West
See all activities in Big Pine Key

Frequently asked questions

How much does a Big Pine Key holiday package cost?
You can grab a holiday package to this destination from €354 on Expedia. But how much your holiday 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 hoping to book a cheap Big Pine Key holiday package, consider travelling in August, September and October. You'll typically find lower rates on flights and accommodation during these months — perfect for a budget-friendly getaway.
How many days is enough for Big Pine Key?
To get the most out of a Big Pine Key holiday, we recommend staying for 3 days. Divide your time between visiting Loggerhead Beach, Sandspur Beach and other top attractions, in addition to experiencing neighbourhoods like Punta Brisa and Long Beach Estates. If you've got some time to spare, include a day trip in your Big Pine Key holiday itinerary.
Is it worth booking a holiday package to Big Pine Key?
Whether you're looking to visit major sights such as No Name Key and National Key Deer Refuge Visitor Centre on your Big Pine Key holiday, or coming for its excellent fishing, watersports and walking trails, there's something for everyone here. With so many things to see and do, you'll quickly learn why so many people think Big Pine Key is a good holiday destination.
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 personalise your search by "Property class," "Number of bedrooms," "Traveller 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 holiday as a package?
Expedia holiday 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 holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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 travel: Check your schedule and get your bags packed. Your preferred time of year and the activities available will also help you decide when to holiday in Big Pine Key.
  2. Set your budget: Factor in expenses such as transportation, flights and meals when working out how much to save for your trip to Big Pine Key. Then, pick a hotel that suits your budget, whether that's an economical stay or a high-end getaway.
  3. Decide how long to go away for: Now that you're up to speed on Big Pine Key, you can work out the ideal length of your holiday. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodation: After you've settled on your dates and duration, book the right Big Pine Key holiday package for you.

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