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Big Pine Key Vacation Rentals

1 - 42 of 305 rentals
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Papa's Hideaway #2 - Sun Also Rises - Key West, FL Vacation Rental
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Papa's Hideaway #4 - Islands in the Stream - Key West, FL Vacation Rental
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Papa's Hideaway  - Garden of Eden - Key West, FL Vacation Rental
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Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
279 305 - - - - - - - - - - - - - - 238
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
445 - - 474 341 216 205 - - - - - - - - - -
Casa Atlantic - Key West, FL Vacation Rental

Casa Atlantic

Key West, FL
3 Bed 3 Bath Sleeps 9
- 336 335 330 278 213 221 261 267 266 251 242 251 252 255 271 263
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
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Canalside in the Keys - Key West, FL Vacation Rental

Canalside in the Keys

Key West, FL
2 Bed 2 Bath Sleeps 6
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Dream in the Keys - Key Colony Beach, FL Vacation Rental

Dream in the Keys

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - - - - 206 215 216 216 214 215 215 214 214
 The Dolphin - Key Largo, FL Vacation Rental

The Dolphin

Key Largo, FL
1 Bed 1 Bath Sleeps 2
117 - - 132 131 122 122 116 - - - 114 118 121 115 - -
Casa Bonita @ Duval Square R1 - Key West, FL Vacation Rental
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Casa Caribe @ Duval Square - Key West, FL Vacation Rental

Casa Caribe @ Duval Square

Key West, FL
2 Bed 2.5 Bath Sleeps 6
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Double Delight  - Key West, FL Vacation Rental

Double Delight

Key West, FL
0 Bed 1 Bath Sleeps 4
- - - 164 149 140 - - - - - - - - - - -
The Gold Medallion - Key Largo, FL Vacation Rental

The Gold Medallion

Key Largo, FL
1 Bed 1 Bath Sleeps 2
145 156 156 164 155 143 144 144 147 148 143 141 140 142 143 146 147
Bougainvillea - Key West, FL Vacation Rental

Bougainvillea

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - - 139 143 138 - - - - - - - - - -
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - 138 147 142 135 - - - 135 143 135 - - - -
Southern Cross - Tropical Village - Key West, FL Vacation Rental
- - - - 290 216 - - - - - - - - - - -
Gecko Grotto - Key West, FL Vacation Rental

Gecko Grotto

Key West, FL
0 Bed 1 Bath Sleeps 2
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Helen's Hideaway - Key West, FL Vacation Rental

Helen's Hideaway

Key West, FL
2 Bed 2 Bath Sleeps 6
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Seaport Suite - Key West, FL Vacation Rental

Seaport Suite

Key West, FL
4 Bed 3 Bath Sleeps 12
- - - 565 - 491 496 - - - - 432 - - - - -
Casa Cubana @ Duval Square R14 - Key West, FL Vacation Rental
- - 345 403 335 - - - - - - - - - - - -
Papa's Hideaway #3 - For Whom the Bell Tolls - Key West, FL Vacation Rental
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Casa Key West @ Duval Square - Key West, FL Vacation Rental
- - - 537 488 394 386 - - - - - 406 - - - -
Commodore's Cove - Key West, FL Vacation Rental

Commodore's Cove

Key West, FL
4 Bed 4 Bath Sleeps 12
- - - 565 - - 496 495 - - - 432 - - - - -
The Salty Seahorse - Key Largo, FL Vacation Rental

The Salty Seahorse

Key Largo, FL
1 Bed 1 Bath Sleeps 2
117 - - - 125 122 122 116 - - 128 133 131 134 135 138 139
Sunset Canal: Rose Pink - Key Largo, FL Vacation Rental

Sunset Canal: Rose Pink

Key Largo, FL
3 Bed 2 Bath Sleeps 6
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Secret Garden - Key West, FL Vacation Rental

Secret Garden

Key West, FL
2 Bed 1 Bath Sleeps 4
- 219 218 215 182 174 172 - - - - - - - 198 221 214
Passover Cottage - Key West, FL Vacation Rental

Passover Cottage

Key West, FL
2 Bed 2 Bath Sleeps 6
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Duval Dreamin' - Key West, FL Vacation Rental

Duval Dreamin'

Key West, FL
2 Bed 2 Bath Sleeps 6
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Caribbean Dreams - Key West, FL Vacation Rental

Caribbean Dreams

Key West, FL
0 Bed 1 Bath Sleeps 2
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Casa Hermosa - Key West, FL Vacation Rental

Casa Hermosa

Key West, FL
2 Bed 2 Bath Sleeps 5
- - - - - 162 172 171 176 174 164 158 164 165 167 177 172
Caribbean Fling - Key West, FL Vacation Rental

Caribbean Fling

Key West, FL
2 Bed 1.5 Bath Sleeps 6
- 213 213 225 195 170 172 171 176 174 164 158 164 165 167 177 172
The Shark Pup - Key Largo, FL Vacation Rental

The Shark Pup

Key Largo, FL
1 Bed 1 Bath Sleeps 2
136 148 147 154 146 135 136 136 139 140 135 133 131 134 135 138 139
Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
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Bay Harbor View - Key West, FL Vacation Rental

Bay Harbor View

Key West, FL
5 Bed 3 Bath Sleeps 18
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Paradise Palms - Key West, FL Vacation Rental

Paradise Palms

Key West, FL
2 Bed 2 Bath Sleeps 6
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Rum Cay Suite #304 - Key West, FL Vacation Rental

Rum Cay Suite #304

Key West, FL
2 Bed 2 Bath Sleeps 6
- - - - 165 - - - - - - - - - - - -
Lorelane Lookout - Key Largo, FL Vacation Rental

Lorelane Lookout

Key Largo, FL
4 Bed 2.5 Bath Sleeps 9
114 114 114 117 117 114 114 114 114 114 114 114 114 114 114 114 114
Monroe Suite  - Key West, FL Vacation Rental

Monroe Suite

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - 135 - - - - - - - - - - - - -
Havana Daydream @ Key Cove - Key West, FL Vacation Rental

Havana Daydream @ Key Cove

Key West, FL
4 Bed 4 Bath Sleeps 10
- 273 272 277 253 237 240 260 263 263 256 251 256 256 257 265 261
Waterfall 4 - Key West, FL Vacation Rental

Waterfall 4

Key West, FL
0 Bed 1 Bath Sleeps 2
- - - 126 - - - - - - - - - - - - -
A Key Escape - Key West, FL Vacation Rental

A Key Escape

Key West, FL
3 Bed 2.5 Bath Sleeps 8
551 - - 611 539 - - - - - - 477 491 - - - -
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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, FL

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, FL

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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