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Big Pine Key Vacation Rentals

1 - 42 of 66 rentals
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Marathon Waterfront Recreational Paradise - Marathon, FL Vacation Rental
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Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
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Sunny Conch Getaway - Key West, FL Vacation Rental

Sunny Conch Getaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- 190 195 195 195 195 195 190 190 190 190 190 190 190 195 195 195
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- 295 - - - - 340 315 315 315 315 295 - - - - 285
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - - 270 - - - 355 375 375 355 - - - - 395
The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
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Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - 185 - - - - - - - - - - -
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
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Sunnyside Canal  - Key Colony Beach, FL Vacation Rental

Sunnyside Canal

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 6
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White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
265 265 265 265 265 265 265 235 235 235 235 235 235 235 245 245 245
Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
125 125 125 125 125 125 125 99 99 99 99 99 99 99 99 99 99
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
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The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Landings of Largo Gem - Key Largo, FL Vacation Rental

Landings of Largo Gem

Key Largo, FL
2 Bed 2 Bath Sleeps 7 (4 Adults Max)
75 75 75 75 75 70 - - - - - - - 70 65 65 65
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
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Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
- - 165 170 170 145 - - - - - - - - - - -
Lower Keys Backcountry Escape - Sugarloaf Key, FL Vacation Rental
- - - - - 99 115 99 99 99 99 99 99 99 99 99 99
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - - 170 195 195 195
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
- 225 225 225 225 260 260 195 195 195 195 195 195 - - - -
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- - - - - - 120 - - - - - - - 125 130 130
Boater's Dream Come True - Marathon, FL Vacation Rental

Boater's Dream Come True

Marathon, FL
4 Bed 2.5 Bath Sleeps 12
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Fishing and Kayaking Dream Cove - Marathon, FL Vacation Rental
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Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - - 315 330 285 - - - - - - - - - - -
Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
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Fisher's Paradise - Key Colony Beach, FL Vacation Rental

Fisher's Paradise

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - 160 170
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
170 170 170 170 170 170 170 160 160 160 160 160 160 160 160 - -
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- 180 - - - - 180 - - - - - - 145 - - -
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
- - - - - 140 150 140 140 140 140 140 120 - - - -
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
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Ninth Street Splendor - Key Colony Beach, FL Vacation Rental
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Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
- - - - - - - - - - - - - 99 125 - -
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - - 240 250 250 265 265 265
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- - - - - - 140 - - - - - - - 145 150 150
Sunlit Serenity - Key Colony Beach, FL Vacation Rental

Sunlit Serenity

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
170 170 170 170 170 170 170 160 160 160 150 - - - - - -
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
- - 115 120 120 120 120 99 99 99 99 99 99 99 99 99 99
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
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Comfort in the Keys - Key Colony Beach, FL Vacation Rental
- 170 170 170 170 170 170 150 - - - - - - - - -
Downhome Cabin by the Canal - Key Colony Beach, FL Vacation Rental
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Floridian Fanfare - Key Colony Beach, FL Vacation Rental

Floridian Fanfare

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
- 145 145 145 135 - - - - - - - - - - - -
White Dunes Retreat  - Key Colony Beach, FL Vacation Rental
- 170 - - - - - - - 160 170 160 - - - - -
Breezy Palms - Key Colony Beach, FL Vacation Rental

Breezy Palms

Key Colony Beach, FL
4 Bed 4 Bath Sleeps 9
- - - - - 135 - - - - - - - - - - -
Page 1 of 2

About Big Pine Key

What do you think of when you hear someone mention the beautiful Florida Keys? Sunshine and palm trees? Seafood and Key lime pie? What about Key deer and sweeping ocean views? Big Pine Key, as its name suggests, is big on character and charm, and it fits right in with the grace and glamor you expect from South Florida destinations. The best part is that you can stay in a stunning vacation home that allows you to enjoy the true beauty of this area!

Where is Big Pine Key, FL?

Situated off of mile marker 30 on U.S. 1, Big Pine Key is a roughly 5,000-person community in Monroe County in the lower Florida Keys. U.S. 1, also known as the Overseas Highway, is the only way to access the island unless you're traveling by sea. Recognized as one of the larger keys, the community is named after its native pines. 

Big Pine Key is one of the 1,700 islands (many of which are uninhabitable) that compose the Florida Keys, and it shares several features with these other islands - namely its beauty and diversity. Big Pine Key, however, separates itself from the other island communities in that it is home to the endangered species of Key deer, which are about the size of a medium dog. Found all around the island, these knee-high animals are friendly and adorable and add a surprising touch to the island. 

Things to Do in Big Pine Key

The National Key Deer Refuge is an 8,500-acre refuge of mostly undeveloped pinelands. Home to hundreds of species of flora and fauna, including more than 20 endangered and threatened plant and animal species, the refuge offers the opportunity for you explore the nature specific to this area of Florida. Visitors are invited to fish and engage in environmental education. 

Blue Hole is another area that boasts an opportunity for exploration. The only freshwater lake in the Florida Keys, this spot is an abandoned rock quarry that is home to lots of wildlife, including alligators, birds, snakes, and green iguanas. Hike around this area for a chance to spot a colorful bird or bright iguana. 

Snorkeling and diving are favorite pastimes around these parts. There are several places that will accommodate day and night dive and snorkel trips for those less-experienced travelers. The 210-foot wreck of Adolphus Busch, Sr. is easily accessible from Big Pine Key, as is the Looe Key coral reef, part of the Florida Keys National Marine Sanctuary. In fact, every year, an underwater music festival is held at the coral reef. Attendees are invited to explore the last living coral reef in the continental United States as they sway and swim to a sub-sea concert. 

Day Trips from Big Pine Key

Just a little more than two dozen miles away lies the island chain of Marathon. With its mangrove and coral reefs, it boasts diverse landscapes and wildlife befitting of a gorgeous Sunshine State destination. 

Fewer than 30 miles away sits the renowned Key West. Characterized by a lively arts culture and tons of outdoor activities, this ecotourist-friendly city will wow you with its beauty and charm.

When Florida is calling your name and you just can't shake that desire for a tropical getaway, give Big Pine Key and our beautiful vacation rentals a try. You'll find yourself leaving with more than just a nice tan: you'll take with you a lifetime of fun-in-the-sun memories.

Photo credit: Thomas James Caldwell via Flickr

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