Vacation Rentals & Apartments in Big Pine Key

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169 apartments

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$172

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$114

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

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$287

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$252

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$140

Island Time (both halves of duplex)

Big Pine Key house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$235

Our Island Thing

Big Pine Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$277

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$147

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$267

PARADISE IN YOUR HANDS

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$218

Large Home near Beach & Key West

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$446

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Responds fast! avg. 2 hours 40 minutes

Price per night from

$172

Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel,

Big Pine Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Big Pine Bungalow: Serene Backyard Oasis, Pool/Spa, Expansive Canal-Facing Deck

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Responds fast! avg. 2 hours 40 minutes

Price per night from

$119

Responds fast! avg. 2 hours 40 minutes

Price per night from

$115

Big Pine Key/Hot tub/Canal Home/updated

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$228

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

$240

Palmetto Retreat

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$143

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$773

Sharkys Island Paradise

Big Pine Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$258

Responds fast! avg. 2 hours 40 minutes

Price per night from

$179

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$170

Responds fast! avg. 2 hours 40 minutes

Price per night from

$126

Great rentals within 20 miles that match your search

Conch Out

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$193

5 O'Clock Somewhere

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$143

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

$687

Bahia Azul

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$268

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

$764

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$153

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

$161

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“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!

Price per night from

$573

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$790

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$621

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$500

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

Price per night from

$1,145

Bow Channel Manor

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$257

Viewing 38 of 169
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

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