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Big Pine Key Vacation Rentals

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58 rentals in Big Pine Key.
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Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve, vacation rental in Big Pine Key
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve, vacation rental in Big Pine Key
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve, vacation rental in Big Pine Key

Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tiki Beach, 4 bedroom, Ocean front house, heated Pool/Spa, beach, vacation rental in Big Pine Key
Tiki Beach, 4 bedroom, Ocean front house, heated Pool/Spa, beach, vacation rental in Big Pine Key
Tiki Beach, 4 bedroom, Ocean front house, heated Pool/Spa, beach, vacation rental in Big Pine Key

Tiki Beach, 4 bedroom, Ocean front house, heated Pool/Spa, beach

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!, vacation rental in Big Pine Key
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!, vacation rental in Big Pine Key
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!, vacation rental in Big Pine Key

Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, vacation rental in Big Pine Key
2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, vacation rental in Big Pine Key
2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, vacation rental in Big Pine Key

2/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BIg Pine Key New House 75 ft dock  250 feet from open waters of Pine Channel, vacation rental in Big Pine Key
BIg Pine Key New House 75 ft dock  250 feet from open waters of Pine Channel, vacation rental in Big Pine Key
BIg Pine Key New House 75 ft dock  250 feet from open waters of Pine Channel, vacation rental in Big Pine Key

BIg Pine Key New House 75 ft dock 250 feet from open waters of Pine Channel

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tropical Caribbean Wonderland, vacation rental in Big Pine Key
Tropical Caribbean Wonderland, vacation rental in Big Pine Key
Tropical Caribbean Wonderland, vacation rental in Big Pine Key

Tropical Caribbean Wonderland

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT, vacation rental in Big Pine Key
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT, vacation rental in Big Pine Key
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT, vacation rental in Big Pine Key

SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mickey and Lynn's House of Windows, vacation rental in Big Pine Key
Mickey and Lynn's House of Windows, vacation rental in Big Pine Key
Mickey and Lynn's House of Windows, vacation rental in Big Pine Key

Mickey and Lynn's House of Windows

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spend your Fall in the Florida Keys. Warm weather without the crowds!, vacation rental in Big Pine Key
Spend your Fall in the Florida Keys. Warm weather without the crowds!, vacation rental in Big Pine Key
Spend your Fall in the Florida Keys. Warm weather without the crowds!, vacation rental in Big Pine Key

Spend your Fall in the Florida Keys. Warm weather without the crowds!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Florida Keys Pine Channel Water Front - Deep Canal

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, vacation rental in Big Pine Key
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, vacation rental in Big Pine Key
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, vacation rental in Big Pine Key

Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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As Seen on  BEACH HUNTERS Sn7 Ep5  Feel like you are on your own private island!, vacation rental in Big Pine Key
As Seen on  BEACH HUNTERS Sn7 Ep5  Feel like you are on your own private island!, vacation rental in Big Pine Key
As Seen on  BEACH HUNTERS Sn7 Ep5  Feel like you are on your own private island!, vacation rental in Big Pine Key

As Seen on BEACH HUNTERS Sn7 Ep5 Feel like you are on your own private island!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Home in The Fabulous Florida Keys!, vacation rental in Big Pine Key
Waterfront Home in The Fabulous Florida Keys!, vacation rental in Big Pine Key
Waterfront Home in The Fabulous Florida Keys!, vacation rental in Big Pine Key

Waterfront Home in The Fabulous Florida Keys!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Open Water and Sunset Views Pool House in the Florida Keys, vacation rental in Big Pine Key
Open Water and Sunset Views Pool House in the Florida Keys, vacation rental in Big Pine Key
Open Water and Sunset Views Pool House in the Florida Keys, vacation rental in Big Pine Key

Open Water and Sunset Views Pool House in the Florida Keys

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tropical Beauty 3 BR Retreat -Pool-Dock-Tiki Hut, vacation rental in Big Pine Key
Tropical Beauty 3 BR Retreat -Pool-Dock-Tiki Hut, vacation rental in Big Pine Key
Tropical Beauty 3 BR Retreat -Pool-Dock-Tiki Hut, vacation rental in Big Pine Key

Tropical Beauty 3 BR Retreat -Pool-Dock-Tiki Hut

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Fisherman's Paradise in the Heart of Big Pine Key , vacation rental in Big Pine Key
Fisherman's Paradise in the Heart of Big Pine Key , vacation rental in Big Pine Key
Fisherman's Paradise in the Heart of Big Pine Key , vacation rental in Big Pine Key

Fisherman's Paradise in the Heart of Big Pine Key

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lower Keys Retreat....., vacation rental in Big Pine Key
Lower Keys Retreat....., vacation rental in Big Pine Key
Lower Keys Retreat....., vacation rental in Big Pine Key

Lower Keys Retreat.....

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Prime Time 2 - Charming Canal Front Duplex, Quick Trip to South Pine Channel And, vacation rental in Big Pine Key
Prime Time 2 - Charming Canal Front Duplex, Quick Trip to South Pine Channel And, vacation rental in Big Pine Key
Prime Time 2 - Charming Canal Front Duplex, Quick Trip to South Pine Channel And, vacation rental in Big Pine Key

Prime Time 2 - Charming Canal Front Duplex, Quick Trip to South Pine Channel And

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel, vacation rental in Big Pine Key
New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel, vacation rental in Big Pine Key
New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel, vacation rental in Big Pine Key

New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lower Keys Retreat....., vacation rental in Big Pine Key
Lower Keys Retreat....., vacation rental in Big Pine Key
Lower Keys Retreat....., vacation rental in Big Pine Key

Lower Keys Retreat.....

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy & Comfortable 2/2 on clean canal with easy ocean and gulf access!, vacation rental in Big Pine Key
Cozy & Comfortable 2/2 on clean canal with easy ocean and gulf access!, vacation rental in Big Pine Key
Cozy & Comfortable 2/2 on clean canal with easy ocean and gulf access!, vacation rental in Big Pine Key

Cozy & Comfortable 2/2 on clean canal with easy ocean and gulf access!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key

Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Welcome to Casa Del Mar  ***********, vacation rental in Big Pine Key
Welcome to Casa Del Mar  ***********, vacation rental in Big Pine Key
Welcome to Casa Del Mar  ***********, vacation rental in Big Pine Key

Welcome to Casa Del Mar ***********

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Waterfront Home in The Fabulous Florida Keys!, vacation rental in Big Pine Key
Waterfront Home in The Fabulous Florida Keys!, vacation rental in Big Pine Key
Waterfront Home in The Fabulous Florida Keys!, vacation rental in Big Pine Key

Waterfront Home in The Fabulous Florida Keys!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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CANAL FRONT HOME IN BIG PINE KEY, vacation rental in Big Pine Key
CANAL FRONT HOME IN BIG PINE KEY, vacation rental in Big Pine Key
CANAL FRONT HOME IN BIG PINE KEY, vacation rental in Big Pine Key

CANAL FRONT HOME IN BIG PINE KEY

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Tropical Waterfront Pool Getaway, vacation rental in Big Pine Key
Tropical Waterfront Pool Getaway, vacation rental in Big Pine Key
Tropical Waterfront Pool Getaway, vacation rental in Big Pine Key

Tropical Waterfront Pool Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large Home near Beach & Key West, vacation rental in Big Pine Key
Large Home near Beach & Key West, vacation rental in Big Pine Key
Large Home near Beach & Key West, vacation rental in Big Pine Key

Large Home near Beach & Key West

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Quaint Florida Keys home
3 bed 1.5 bath on canal, vacation rental in Big Pine Key
Quaint Florida Keys home
3 bed 1.5 bath on canal, vacation rental in Big Pine Key
Quaint Florida Keys home
3 bed 1.5 bath on canal, vacation rental in Big Pine Key

Quaint Florida Keys home 3 bed 1.5 bath on canal

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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2 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key
2 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key
2 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key

2 bedroom accommodation in Big Pine Key

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Prince`s Keys Serenity, vacation rental in Big Pine Key
Prince`s Keys Serenity, vacation rental in Big Pine Key
Prince`s Keys Serenity, vacation rental in Big Pine Key

Prince`s Keys Serenity

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean, vacation rental in Big Pine Key
Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean, vacation rental in Big Pine Key
Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean, vacation rental in Big Pine Key

Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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PRIME TIME - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key
PRIME TIME - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key
PRIME TIME - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key

PRIME TIME - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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PRIME TIME 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And, vacation rental in Big Pine Key
PRIME TIME 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And, vacation rental in Big Pine Key
PRIME TIME 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And, vacation rental in Big Pine Key

PRIME TIME 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Island Time (both halves of duplex), vacation rental in Big Pine Key
Island Time (both halves of duplex), vacation rental in Big Pine Key
Island Time (both halves of duplex), vacation rental in Big Pine Key

Island Time (both halves of duplex)

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Charming Elevated Waterfront Home, vacation rental in Big Pine Key
Charming Elevated Waterfront Home, vacation rental in Big Pine Key
Charming Elevated Waterfront Home, vacation rental in Big Pine Key

Charming Elevated Waterfront Home

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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3 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key
3 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key
3 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key

3 bedroom accommodation in Big Pine Key

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Water's Edge, vacation rental in Big Pine Key
Water's Edge, vacation rental in Big Pine Key
Water's Edge, vacation rental in Big Pine Key

Water's Edge

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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3 Bed 2 bath home located on No Name Key, vacation rental in Big Pine Key
3 Bed 2 bath home located on No Name Key, vacation rental in Big Pine Key
3 Bed 2 bath home located on No Name Key, vacation rental in Big Pine Key

3 Bed 2 bath home located on No Name Key

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Palmetto Retreat, vacation rental in Big Pine Key
Palmetto Retreat, vacation rental in Big Pine Key
Palmetto Retreat, vacation rental in Big Pine Key

Palmetto Retreat

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Hideaway Bay, vacation rental in Big Pine Key
Hideaway Bay, vacation rental in Big Pine Key
Hideaway Bay, vacation rental in Big Pine Key

Hideaway Bay

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Tropical Getaway in the Florida Keys, vacation rental in Big Pine Key
Tropical Getaway in the Florida Keys, vacation rental in Big Pine Key
Tropical Getaway in the Florida Keys, vacation rental in Big Pine Key

Tropical Getaway in the Florida Keys

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Our Island Thing, vacation rental in Big Pine Key
Our Island Thing, vacation rental in Big Pine Key
Our Island Thing, vacation rental in Big Pine Key

Our Island Thing

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW, vacation rental in Big Pine Key
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW, vacation rental in Big Pine Key
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW, vacation rental in Big Pine Key

Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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2 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key
2 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key
2 bedroom accommodation in Big Pine Key, vacation rental in Big Pine Key

2 bedroom accommodation in Big Pine Key

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Island Time 1 (half of duplex), vacation rental in Big Pine Key
Island Time 1 (half of duplex), vacation rental in Big Pine Key
Island Time 1 (half of duplex), vacation rental in Big Pine Key

Island Time 1 (half of duplex)

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Waterfront Keys Cottage 'Del Boca Vista', vacation rental in Big Pine Key
Waterfront Keys Cottage 'Del Boca Vista', vacation rental in Big Pine Key
Waterfront Keys Cottage 'Del Boca Vista', vacation rental in Big Pine Key

Waterfront Keys Cottage 'Del Boca Vista'

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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PARADISE IN YOUR HANDS, vacation rental in Big Pine Key
PARADISE IN YOUR HANDS, vacation rental in Big Pine Key
PARADISE IN YOUR HANDS, vacation rental in Big Pine Key

PARADISE IN YOUR HANDS

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Big Pine Latitude Adjustment, vacation rental in Big Pine Key
Big Pine Latitude Adjustment, vacation rental in Big Pine Key
Big Pine Latitude Adjustment, vacation rental in Big Pine Key

Big Pine Latitude Adjustment

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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12
Frequently Asked Questions about Big Pine Key





Big Pine Key Vacation Rental
Big Pine Key and its neighboring islands are some of the most popular vacation destinations for families who want to rent a beachfront house or condo. The climate in this part of Florida is delightful and very similar to the warm and pleasant climates of the Caribbean. The crystal blue waters and the white sandy beaches in Big Pine Key make this an impressive location for your next vacation rental.
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Big Pine Key Vacation Rental
Big Pine Key and its neighboring islands are some of the most popular vacation destinations for families who want to rent a beachfront house or condo. The climate in this part of Florida is delightful and very similar to the warm and pleasant climates of the Caribbean. The crystal blue waters and the white sandy beaches in Big Pine Key make this an impressive location for your next vacation rental.
Things to Do
Big Pine Key is a fantastic place to come if you want to get away from all the troubles and stress of day-to-day life. The vacation houses and condos available here are designed for rest and relaxation. The main appeal of Big Pine Key is the tranquil environment and beautiful scenery. There are plenty of outdoor activities that you can enjoy when you’re not in your rental home, such as fishing, walking and biking, and seeking out wildlife.
Family Fun
If you’re visiting Big Pine Key with children, there are numerous wonderful activities that will get them out of the rental home for the day. The Theater of the Sea and the National Key Deer Refuge are great options for the whole family. If you would like to spot some of the many alligators that reside in the area, then you should head to the Blue Hole.
Delicious Dining in Big Pine Key
If you’re staying in a vacation home in Big Pine Key, you may choose to dine in and enjoy a quiet intimate or pizza with the family. There are many local groceries where you can purchase fresh seafood and produce to prepare a meal in your condo or villa. However, if you do fancy a meal out, you can take a trip to Rob’s Island Grill, The Big Pine Restaurant, or The China Garden. All of these restaurants are local and provide culinary delights.
Benefits of Big Pine Key Rentals
Unlike a hotel, staying in a Big Pine Key vacation rental provides you with complete privacy and tranquility during your vacation. Enjoy the space and security you can get from your own beautiful rental home.