Vacation Rentals & Apartments in Big Pine Key

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254 apartments

(1) Excellent 

20

Fisherman's Paradise in the Heart of Big Pine Key

Florida Keys / Big Pine Key

Big Pine Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly

Price per night from

$113

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$113

10

Big Pine 2/2 ,Water Views

Florida Keys / Big Pine Key

Big Pine Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$131

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$131

16

Charming Elevated Waterfront Home

Florida Keys / Big Pine Key

Big Pine Key house

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$163

Responds fast!
avg. 3 hours 2 minutes

Price per night from

$163

24

Sunrise Drive

Florida Keys / Big Pine Key

Big Pine Key house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 mi
  • Suitable for children age 5+

Price per night from

$198

Responds fast!
avg. 3 hours 4 minutes

Price per night from

$198

13

3 bedroom canal front home minutes from open Water!

Florida Keys / Big Pine Key

Big Pine Key house

3 10 30 nights min

  • 3 bedrooms
  • sleeps 10
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$171

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$171

16

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

Florida Keys / Big Pine Key

Big Pine Key house

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$201

Price per night from

$201

(3) Average 

19

Waterfront Home in The Fabulous Florida Keys!

Florida Keys / Big Pine Key

Big Pine Key house

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 mi
  • Child Friendly

Price per night from

$286

Price per night from

$286

(1) Very Good 

13

RV Lifestyle, close to Key West

Florida Keys / Big Pine Key

Big Pine Key caravan/mobile home

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$115

Price per night from

$115

24

**Winter Promo** Experience the Keys like a Local at this Spacious Canal Front H

Florida Keys / Big Pine Key

Big Pine Key house

3 7 28 nights min

  • 3 bedrooms
  • sleeps 7
  • 28 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$162

Responds fast!
avg. 17 minutes

Price per night from

$162

27

Island Time (both halves of duplex)

Florida Keys / Big Pine Key

Big Pine Key house

5 10 30 nights min

  • 5 bedrooms
  • sleeps 10
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$197

Price per night from

$197

(10) Excellent 

17

Reel Paradise - Big Pine Key

Florida Keys / Big Pine Key

Big Pine Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$161

Price per night from

$161

12

Hideaway Bay

Florida Keys / Big Pine Key

Big Pine Key house

2 4 31 nights min

  • 2 bedrooms
  • sleeps 4
  • 31 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$105

Price per night from

$105

28

Florida Keys Fisherman and Divers Paradise

Florida Keys / Big Pine Key

Big Pine Key house

4 12 30 nights min

  • 4 bedrooms
  • sleeps 12
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$287

Price per night from

$287

16

Sparkling canalfront house surrounded by palms

Florida Keys / Big Pine Key

Big Pine Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$134

Price per night from

$134

(1)  

16

Our Island Thing

Florida Keys / Big Pine Key

Big Pine Key house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$200

Price per night from

$200

15

Island Time 1 (half of duplex)

Florida Keys / Big Pine Key

Big Pine Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$87

Price per night from

$87

12

Lost In Paradise

Florida Keys / Big Pine Key

Big Pine Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$133

Price per night from

$133

10

Blue Heron

Florida Keys / Big Pine Key

Big Pine Key house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$86

Price per night from

$86

16

*Winter Promo*Unwind at a waterfront home, a short drive to fun, shops, dining &

Florida Keys / Big Pine Key

Big Pine Key house

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$150

Responds fast!
avg. 17 minutes

Price per night from

$150

16

Island Time 2 (half of duplex)

Florida Keys / Big Pine Key

Big Pine Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$93

Price per night from

$93

(1) Excellent 

14

Breeze Swept

Florida Keys / Big Pine Key

Big Pine Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$193

Price per night from

$193

35

Caribbean Cove

Florida Keys / Big Pine Key

Big Pine Key house

2 9 28 nights min

  • 2 bedrooms
  • sleeps 9
  • 28 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$99

Price per night from

$99

Great rentals within 20 miles that match your search

Distance approx 8.51 km from Big Pine Key Show on Map

13

Waterside Bay

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 28 nights min

  • 3 bedrooms
  • sleeps 6
  • 28 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$196

Price per night from

$196

Distance approx 2.08 km from Big Pine Key Show on Map

(1) Excellent 

15

Barry Beach (weekly Rental)

Lower Keys / Little Torch Key

Little Torch Key house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$449

Price per night from

$449

Distance approx 17.26 km from Big Pine Key

31

P81 ~ Cozy Cove Marathon ~ Sombrero Beach Home 3 BEDROOM

Florida Keys / Marathon

Marathon house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool

Price per night from

$220

Price per night from

$220

Distance approx 5.74 km from Big Pine Key Show on Map

19

Gone Fishing

Lower Keys / Summerland Key

Summerland Key house

3 6 28 nights min

  • 3 bedrooms
  • sleeps 6
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$211

Price per night from

$211

Distance approx 18.75 km from Big Pine Key

8

Aparment 1

Florida Keys / Marathon

Marathon apartment

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$314

Price per night from

$314

Distance approx 18.64 km from Big Pine Key

(8) Excellent 

76

NATURES FINEST ADDRESS, Breathtaking Views, Private, Tranquil, Book now

Florida Keys / Marathon

Marathon house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
“We thoroughly enjoyed our stay.” My wife and I would highly recommend The Sunrise Getaway House in Marathon. The accomodations were everything we wanted in our trip and more. The location was excellant and the view fantastic! We also found the coop
…see more

Price per night from

$428

Price per night from

$428

Distance approx 8.17 km from Big Pine Key Show on Map

14

Egret's Landing

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$100

Price per night from

$100

Distance approx 9.42 km from Big Pine Key

11

Pink House

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$167

Price per night from

$167

Distance approx 7.84 km from Big Pine Key Show on Map

8

Quiet Waters

Florida Keys / Cudjoe Key

Cudjoe Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$90

Price per night from

$90

Distance approx 13.19 km from Big Pine Key

12

Green Turtle Landing

Florida Keys / Sugarloaf

Sugarloaf house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$140

Price per night from

$140

Distance approx 1.64 km from Big Pine Key Show on Map

16

Conch Out

Lower Keys / Little Torch Key

Little Torch Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$140

Price per night from

$140

Distance approx 3.4 km from Big Pine Key Show on Map

14

Tree House

Florida Keys / Ramrod Key

Ramrod Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$100

Price per night from

$100

Distance approx 3.36 km from Big Pine Key Show on Map

17

Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys

Florida Keys / Ramrod Key

Ramrod Key house

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$129

Price per night from

$129

Distance approx 3.14 km from Big Pine Key Show on Map

27

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

Lower Keys / Summerland Key

Summerland Key house

5 10 30 nights min

  • 5 bedrooms
  • sleeps 10
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$762

Price per night from

$762

Distance approx 2.23 km from Big Pine Key Show on Map

(1) Excellent 

18

Pirates Pointe

Lower Keys / Little Torch Key

Little Torch Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$120

Price per night from

$120

Distance approx 16.04 km from Big Pine Key

53

Keys Cove House 8

Marathon / Marathon Shores

Marathon Shores house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$571

Responds fast!
avg. 51 minutes

Price per night from

$571

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.