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Vacation Rentals & Apartments in Big Pine Key

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Price: high to low

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243 apartments

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 45 minutes

Price per night from

$184

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 48 minutes

Price per night from

$113

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 55 minutes

Price per night from

$198

Big Pine 2/2 ,Water Views

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 44 minutes

Price per night from

$144

Waterfront Home in The Fabulous Florida Keys!

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$286

Blue Heron

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$105

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 28 minutes

Price per night from

$218

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$119

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$214

Our Island Thing

Big Pine Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$216

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$123

Hideaway Bay

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$112

Reel Paradise - Big Pine Key

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$161

Breeze Swept

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$206

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$184

Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$121

Large Home near Beach & Key West

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 13

Price per night from

$454

Prime Time 2 - Charming Canal Front Duplex, Quick Trip to South Pine Channel And

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$116

Water's Edge

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$135

Great rentals within 20 miles that match your search

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$863

MARATHON MAJIC

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$324

Get out of the cold Feb.5-12, 2018 in Florida Keys at Marathon,The Hammocks

Marathon Shores villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$557

Salty Anglers, Spacious Sombrero Beach Waterfront 4 Bdrm w/Heated Pool & Dockage

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$941

Grouper Therapy

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$155

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$166

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$276

Venture Out 128

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$221

Coconut Cay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$166

Buccaneer Boathouse

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$117

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$203

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$150

Manatee Bay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$122

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$183

Casa Rosa

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$124

Paradise Bay

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$121

Cudjoe Cottage

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$131

Conch Out

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$155

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$142

Viewing 38 of 243
rentals in Big Pine Key

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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.

Top Destination reviews

Fisherman's Paradise in the Heart of Big Pine Key
Perfect place for fisherman and their families.

Home is nicely decorated with some really cool nautical artwork. Key deer come up every evening and morning (don't feed them). The canal and channels are easy to navigate thanks to the owner Matt. There is a neighborhood boat ramp not far away called Eden Pines Boat Ramp, but you'll need someone to drive your trailer back to the house. The back porch area is spacious and very Florida style. Plenty of bed linens and towels and the washer/dryer worked great. Now back to work so I can afford to come back again.see more
Reel Paradise - Big Pine Key
Paradise for reel!

What a pleasure to deal with such a nice homeowner. The Home was perfect, very nice vacation! Highly recommend this Vacation Rental! Perfect for quiet couples or family's. Completely satisfied with the Home, Price and Location is perfect! … see more
Keys Caribbean Retreat
A great place to stay !

This was our first experience renting a house for our vacation instead of a hotel AND one of our best vacation decisions we've ever made. The house was great and Captain Ron and his wife made sure that you had everything you needed. There was more than enough room for the four of us and the outside area by the canal was great for relaxing. Extra bonus , the cute Key Deer came through the yard numerous times every day. Another plus , a family pass is provided for the State Parks. The house is nicely decorated and was spic and span clean when we checked in. You have peace of mind by booking through Trip Advisor, though in the future I wouldn't be concerned with booking directly with Captain Ron. Our security was refunded in a timely fashion. Hopefully in a few years we'll be able to return to the Keys and will definitely rent Captain Ron's house again.see more
Captain Rons Tropical Vacation Hideaway
We had a great trip.

We had a great time while in the Keys. The house had everything we needed. Washer and dryer worked good and it even had a bait freezer to store bait for fishing in. We used the kayak and paddled out of the canal to the bridge to No Name Key. It is a very beautiful area. Captain Ron was very helpful and everything in the house went smoothly. They Key deer were there all the time and very friendly.see more

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