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Price: high to low
Number of reviews
Price per night from
$175
Fisherman's Paradise in the Heart of Big Pine Key
Big Pine Key house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$115
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
Big Pine Key house
3 bedrooms / 3 bathrooms / sleeps 8
Responds fast! avg. 1 hour 35 minutes
Price per night from
$233
Responds fast! avg. 2 hours 7 minutes
Price per night from
$256
Price per night from
$127
Price per night from
$239
Price per night from
$130
Price per night from
$221
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access
Big Pine Key house
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 47 minutes
Price per night from
$119
Responds fast! avg. 2 hours 21 minutes
Price per night from
$348
Prime Time 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And
Big Pine Key house
2 bedrooms / 1 bathroom / sleeps 6
Responds fast! avg. 2 hours 47 minutes
Price per night from
$115
Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean
Big Pine Key house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$233
The Pineapple Cottage - Live Your Best Keys Life, 3 Bedroom Canal Front Home, Do
Big Pine Key house
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 47 minutes
Price per night from
$172
Responds fast! avg. 17 minutes
Price per night from
$229
Great rentals within 20 miles that match your search
Responds fast! avg. 3 hours 59 minutes
Price per night from
$697
Family Retreat-Ocean front home with private pool
Cudjoe Key house
6 bedrooms / 4 bathrooms / sleeps 14
Responds fast! avg. 3 hours 59 minutes
Price per night from
$697
Charming 3bedroom/2bath home in the Florida Keys
Cudjoe Key house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$132
Price per night from
$507
“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!
Responds fast! avg. 3 hours 59 minutes
Price per night from
$581
OUTSTANDING Oceanfront House with Pool and Deep water dockage!!
Marathon house
4 bedrooms / 3 bathrooms / sleeps 10
“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problems. I would highly recommend this rental
Responds fast! avg. 2 hours 50 minutes
Price per night from
$879
Price per night from
$155
30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.
Summerland Key house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$163
Price per night from
$664
“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!
Price per night from
$307
“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!
Responds fast! avg. 1 hour 49 minutes
Price per night from
$115
Dragonfly Lite A Private home in a tropical setting with your own pool to enjoy!
Marathon house
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$320
Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants
Marathon Shores house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$697
Beautiful Beachfront Home w/Heated Pool+45' Dock
Marathon house
3 bedrooms / 3 bathrooms / sleeps 10
“Beautiful Home and Beautiful Beach Across the Street” My family had a fabulous relaxing vacation. The house and amenities were great. We had a beautiful front porch to watch the morning sunrise and beautiful views of Sombrero Beach. The guys enjoyed fishing everyday while the ladies enjoyed the beach. The beach opens at sunrise and closes at sunset. We had great weather and can't wait to return!
Price per night from
$812
Viewing 38 of 172
rentals in Big Pine Key
About Big Pine Key
Big Pine Key, Florida
This may seem like a small island, but it has a big heart. You'll always be welcome in Big Pine Key—and there's always something to do.
Explore this unique part of Monroe County on your next trip and book your vacation rental with FlipKey—that way you'll have the best place to stay!
About Big Pine Key, Florida
Tourists come to Big Pine Key for a bit of sunshine and small town living. You'll quickly become part of the community during your stay, so much so that you may not want to leave!
Embrace the low-key lifestyle and escape from your busy life for a week or two. Feel like a local—grab groceries from Winn-Dixie and explore the shopping center.
There are plenty of restaurants, a Beal's Outlet store and a RadioShack—we bet you didn't think it’d have all of that, did you?
The shopping center is also home to the visitors’ center for the National Key Deer Refuge. It's worth going there to find out more about the area, and the local wildlife.
While it may seem like a sleepy town, it's got pretty wild nightlife—there are restaurants, clubs and bars that stay open until late and have great deals on drinks.
What to do
Visit the Blue Hole—it's an abandoned rock quarry from years ago. It's now filled with fresh water and is a great place to spot the local wildlife, including birds, snakes, alligators and green iguanas.
Seeing those animals makes for a great day out, but the species Big Pine Key is most famous for is Key deer. Head to the refuge, where you'll see the majority of them. They're an endangered species, but they're well looked after here. Don't be shocked at how small they are—they're the size of a large dog, and very cute.
If you've had your fill of nature, try one of the many water sports on offer. You can go boating, fishing, scuba diving snorkeling and more during your stay. Just take your pick!
Looking for a great beach? There are stretches of white sand at Bahia Honda State Park. It's a great place to spend a day.
Top travel tips
As deer are everywhere—including the road—you should pay special attention when driving. They tend to come out at night, so keep your wits about you.
Where there's great fishing, there's great seafood restaurants, and Big Pine Key doesn't disappoint. Try some of the local produce during your stay.
Make sure you check out the flea market, too. It's open on Sundays and has everything you could possibly need during your vacation.
Whether you're here for the beach, hospitality or wildlife, you'll have a great time in Big Pine Key. Explore and discover everything this island has to offer during your stay by booking your rental accommodation on FlipKey.
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