Big Pine Key Vacations 2026 from CA $1,187

Big Pine Key flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

CA $1,187

per person

Dec 6 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Miami (MIA)

Stay at this hotel in Miami Beach. Enjoy free WiFi, beach cabanas (surcharge), and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $11,682

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

Book a stay at this luxury aparthotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

CA $3,008

per person

Nov 1 - Nov 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

Book a stay at this beach hotel in Key West. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.

Rooftop Resort - Clothing Optional - Adult Only

Hollywood Beach

Save 100% on your flight

CA $1,348

per person

Dec 9 - Dec 16

found 12 hours ago

Roundtrip flight included

Montreal (YUL) to Miami (MIA)

Stay at this hotel in Hollywood. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Hollywood Beach and Port Everglades are located nearby.

Park Central South Beach

South Beach

Save 100% on your flight

CA $1,938

per person

Dec 6 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Miami (MIA)

Book a stay at this historic resort in Miami Beach. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.

Top Big Pine Key hotels deals

Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL

CA $127

CA $342 total

Sep 27 - Sep 28

includes taxes & fees

Stay at this cottage in Big Pine Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Blue Hole and Big Pine Key Flea Market are located nearby.

Pool

Pet-friendly

Sunshine Key RV Resort & Marina

38801 Overseas Highway Big Pine Key FL

Get rates

Enjoy a private beach, a marina, and laundry facilities. Popular attractions Bahia Honda State Park and Sandspur Beach are located nearby.

Pool

Kitchen

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

Big Pine Key FL

CA $317

CA $831 total

Sep 28 - Sep 29

includes taxes & fees

Stay at this vacation home in Big Pine Key. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Big Pine Key Flea Market and Coupon Bight Aquatic Preserve are located nearby.

Kitchen

Washer

Isla Bella Beach Resort & Spa

1 Knights Key Boulevard Marathon FL

Free cancellation

Reserve now, pay when you stay

CA $261

CA $377 total

Sep 27 - Sep 28

includes taxes & fees

Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sombrero Beach and Vaca Key are located nearby.

Pool

Spa

Fairfield Inn & Suites by Marriott Marathon Florida Keys

13201 Overseas Hwy Marathon FL

Free cancellation

Reserve now, pay when you stay

CA $190

CA $213 total

Oct 4 - Oct 5

includes taxes & fees

Book a stay at this business-friendly hotel in Marathon. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Sombrero Beach and Captain Hooks Marina and Dive Center are located nearby.

Parmer's Resort

565 Barry Avenue Summerland Key FL

Free cancellation

Reserve now, pay when you stay

CA $203

CA $275 total

Oct 4 - Oct 5

includes taxes & fees

Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Boondocks Grille & Draft House and Blue Hole are located nearby.

On private beach

Pool

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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.

See properties

Frequently asked questions

How much are vacation packages to Big Pine Key?

Travelocity provides package deals to Big Pine Key, including hotels and flights, starting at just CA $1,187. With all the extra cash, you could book some cool tours or possibly even tack on a few extra nights to your exciting adventure.

Where can I get the best vacation package deals for Big Pine Key?

You'll come across an excellent range of Big Pine Key package deals on Travelocity. With no less than 400 air carriers and 665,000 properties around the globe, arranging your ultimate getaway will be simple.

Why should I purchase my Big Pine Key vacation package via Travelocity?

By booking your hotel, flights, activities and car rental altogether, you'll save big bucks as well as precious time. We offer an expert team of customer service specialists available 24/7, and you'll know that you'll always score the best deal in town with our Price Match Guarantee. So, what's stopping you? Book your dream getaway today and get packing!

Will I save money on my Big Pine Key car rental if I book it with my hotel or flight?

Absolutely. And our Big Pine Key vacation packages are the perfect way to do it. With only a few clicks you can save cash and time by combining your bookings. Collect the keys to your rental car and do your vacation your way. Looking for things to do? Add some activities or experiences to your package and make savings on those too.

What is the best time of year to go to Big Pine Key?

You'll nab the lowest hotel prices in and pay more in . It's generally quieter in , while you'll find a lot more fellow visitors to hang out with in . It comes down to how much you're willing to pay, the weather and how well you deal with crowds.

Can I go on vacation to Big Pine Key at this time?

Discover all the info you should know about travel restrictions and quarantine policies before you head for Big Pine Key. Our Covid-19 Travel Advisor is full of advice to help make your vacation relaxed and hassle-free.