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Vacation Rentals & Apartments in Big Pine Key

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172 apartments

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom / 1 bathroom / sleeps 4

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

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 7 minutes

Price per night from

$256

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$127

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$239

Our Island Thing

Big Pine Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$261

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$130

Hideaway Bay

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$129

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 8

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

Large Home near Beach & Key West

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 12

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

Palmetto Retreat

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$145

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

Gorgeous 4/2 Canal Front Home

Big Pine Key villa

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 17 minutes

Price per night from

$229

Water's Edge

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$153

Great rentals within 20 miles that match your search

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

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

OCEANFRONT LUXURY "Mar Azul"

Marathon house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$507

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!

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

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

1 bedroom / 1 bathroom / sleeps 4

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

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$664

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$160

Reef Resort - Peaceful Getaway 204

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

“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

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

Price per night from

$241

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$145

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“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

Conch Out

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

Price per night from

$320

5 O'Clock Somewhere

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$125

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

Bahia Azul

Ramrod Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$261

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

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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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