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Holiday Apartments in Big Pine Key

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

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!, holiday rental in Big Pine Key
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!, holiday rental in Big Pine Key
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!, holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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Tiki Beach, 4 BR/3BA plus loft, ocean front house, pool, grill, dock, holiday rental in Big Pine Key
Tiki Beach, 4 BR/3BA plus loft, ocean front house, pool, grill, dock, holiday rental in Big Pine Key
Tiki Beach, 4 BR/3BA plus loft, ocean front house, pool, grill, dock, holiday rental in Big Pine Key

Tiki Beach, 4 BR/3BA plus loft, ocean front house, pool, grill, dock

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, holiday rental in Big Pine Key
2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, holiday rental in Big Pine Key
2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, holiday rental in Big Pine Key

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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As Seen on  BEACH HUNTERS Sn7 Ep5  Feel like you are on your own private island!, holiday rental in Big Pine Key
As Seen on  BEACH HUNTERS Sn7 Ep5  Feel like you are on your own private island!, holiday rental in Big Pine Key
As Seen on  BEACH HUNTERS Sn7 Ep5  Feel like you are on your own private island!, holiday rental in Big Pine Key

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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BIg Pine Key New House 75 ft dock  250 feet from open waters of Pine Channel, holiday rental in Big Pine Key
BIg Pine Key New House 75 ft dock  250 feet from open waters of Pine Channel, holiday rental in Big Pine Key
BIg Pine Key New House 75 ft dock  250 feet from open waters of Pine Channel, holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tropical Caribbean Wonderland, holiday rental in Big Pine Key
Tropical Caribbean Wonderland, holiday rental in Big Pine Key
Tropical Caribbean Wonderland, holiday rental in Big Pine Key

Tropical Caribbean Wonderland

Holiday Rental House
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, holiday rental in Big Pine Key
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT, holiday rental in Big Pine Key
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT, holiday rental in Big Pine Key

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Florida Keys Pine Channel Water Front - Deep Canal

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

Mickey and Lynn's House of Windows

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Doctors Arm waterfront home with dock and pool going in Fall of 2022, holiday rental in Big Pine Key
Doctors Arm waterfront home with dock and pool going in Fall of 2022, holiday rental in Big Pine Key
Doctors Arm waterfront home with dock and pool going in Fall of 2022, holiday rental in Big Pine Key

Doctors Arm waterfront home with dock and pool going in Fall of 2022

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Listing! Beautiful Canal front , Key Deer and jacuzzi., holiday rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., holiday rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, holiday rental in Big Pine Key
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, holiday rental in Big Pine Key
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, holiday rental in Big Pine Key

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Home in The Fabulous Florida Keys!, holiday rental in Big Pine Key
Waterfront Home in The Fabulous Florida Keys!, holiday rental in Big Pine Key
Waterfront Home in The Fabulous Florida Keys!, holiday rental in Big Pine Key

Waterfront Home in The Fabulous Florida Keys!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pool house with open water and sunset in the Florida Keys, holiday rental in Big Pine Key
Pool house with open water and sunset in the Florida Keys, holiday rental in Big Pine Key
Pool house with open water and sunset in the Florida Keys, holiday rental in Big Pine Key

Pool house with open water and sunset in the Florida Keys

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

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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2/2 Canal Front Home with Great Boating Access! Located in Doctor’s Arm Big Pine, holiday rental in Big Pine Key
2/2 Canal Front Home with Great Boating Access! Located in Doctor’s Arm Big Pine, holiday rental in Big Pine Key
2/2 Canal Front Home with Great Boating Access! Located in Doctor’s Arm Big Pine, holiday rental in Big Pine Key

2/2 Canal Front Home with Great Boating Access! Located in Doctor’s Arm Big Pine

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel, holiday rental in Big Pine Key
New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel, holiday rental in Big Pine Key
New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel, holiday rental in Big Pine Key

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

Holiday Rental House
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, holiday rental in Big Pine Key
Prime Time 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And, holiday rental in Big Pine Key
Prime Time 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And, holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Fisherman's Paradise in the Heart of Big Pine Key , holiday rental in Big Pine Key
Fisherman's Paradise in the Heart of Big Pine Key , holiday rental in Big Pine Key
Fisherman's Paradise in the Heart of Big Pine Key , holiday rental in Big Pine Key

Fisherman's Paradise in the Heart of Big Pine Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lower Keys Retreat....., holiday rental in Big Pine Key
Lower Keys Retreat....., holiday rental in Big Pine Key
Lower Keys Retreat....., holiday rental in Big Pine Key

Lower Keys Retreat.....

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

Lower Keys Retreat.....

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

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Welcome to Casa Del Mar  ***********, holiday rental in Big Pine Key
Welcome to Casa Del Mar  ***********, holiday rental in Big Pine Key
Welcome to Casa Del Mar  ***********, holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Tropical Waterfront Pool Getaway, holiday rental in Big Pine Key
Tropical Waterfront Pool Getaway, holiday rental in Big Pine Key
Tropical Waterfront Pool Getaway, holiday rental in Big Pine Key

Tropical Waterfront Pool Getaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Canal Front Home in Big Pine Key, holiday rental in Big Pine Key
Canal Front Home in Big Pine Key, holiday rental in Big Pine Key
Canal Front Home in Big Pine Key, holiday rental in Big Pine Key

Canal Front Home in Big Pine Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, holiday rental in Big Pine Key
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, holiday rental in Big Pine Key
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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2 bedroom accommodation in Big Pine Key, holiday rental in Big Pine Key
2 bedroom accommodation in Big Pine Key, holiday rental in Big Pine Key
2 bedroom accommodation in Big Pine Key, holiday rental in Big Pine Key

2 bedroom accommodation in Big Pine Key

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

Prince`s Keys Serenity

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

Large Home near Beach & Key West

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Perfect Keys Getaway, holiday rental in Big Pine Key
Perfect Keys Getaway, holiday rental in Big Pine Key
Perfect Keys Getaway, holiday rental in Big Pine Key

Perfect Keys Getaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Gorgeous 4/2 Canal Front Home, holiday rental in Big Pine Key
Gorgeous 4/2 Canal Front Home, holiday rental in Big Pine Key
Gorgeous 4/2 Canal Front Home, holiday rental in Big Pine Key

Gorgeous 4/2 Canal Front Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hideaway Bay, holiday rental in Big Pine Key
Hideaway Bay, holiday rental in Big Pine Key
Hideaway Bay, holiday rental in Big Pine Key

Hideaway Bay

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean, holiday rental in Big Pine Key
Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean, holiday rental in Big Pine Key
Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean, holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
2 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, holiday rental in Big Pine Key
Prime Time 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And, holiday rental in Big Pine Key
Prime Time 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel And, holiday rental in Big Pine Key

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Palmetto Retreat, holiday rental in Big Pine Key
Palmetto Retreat, holiday rental in Big Pine Key
Palmetto Retreat, holiday rental in Big Pine Key

Palmetto Retreat

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Island Time (both halves of duplex), holiday rental in Big Pine Key
Island Time (both halves of duplex), holiday rental in Big Pine Key
Island Time (both halves of duplex), holiday rental in Big Pine Key

Island Time (both halves of duplex)

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, holiday rental in Big Pine Key
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, holiday rental in Big Pine Key
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, holiday rental in Big Pine Key

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SEA FOREVER! Gorgeous Ocean-Front Paradise!, holiday rental in Big Pine Key
SEA FOREVER! Gorgeous Ocean-Front Paradise!, holiday rental in Big Pine Key
SEA FOREVER! Gorgeous Ocean-Front Paradise!, holiday rental in Big Pine Key

SEA FOREVER! Gorgeous Ocean-Front Paradise!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Our Island Thing, holiday rental in Big Pine Key
Our Island Thing, holiday rental in Big Pine Key
Our Island Thing, holiday rental in Big Pine Key

Our Island Thing

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Big Pine Latitude Adjustment, holiday rental in Big Pine Key
Big Pine Latitude Adjustment, holiday rental in Big Pine Key
Big Pine Latitude Adjustment, holiday rental in Big Pine Key

Big Pine Latitude Adjustment

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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New Listing! Beautiful Canal front , Key Deer and jacuzzi., holiday rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., holiday rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Water's Edge, holiday rental in Big Pine Key
Water's Edge, holiday rental in Big Pine Key
Water's Edge, holiday rental in Big Pine Key

Water's Edge

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Pineapple Cottage - Live Your Best Keys Life, 3 Bedroom Canal Front Home, Do, holiday rental in Big Pine Key
The Pineapple Cottage - Live Your Best Keys Life, 3 Bedroom Canal Front Home, Do, holiday rental in Big Pine Key
The Pineapple Cottage - Live Your Best Keys Life, 3 Bedroom Canal Front Home, Do, holiday rental in Big Pine Key

The Pineapple Cottage - Live Your Best Keys Life, 3 Bedroom Canal Front Home, Do

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sweet Dreams in Big Pine Key, holiday rental in Big Pine Key
Sweet Dreams in Big Pine Key, holiday rental in Big Pine Key
Sweet Dreams in Big Pine Key, holiday rental in Big Pine Key

Sweet Dreams in Big Pine Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Island Time 1 (half of duplex), holiday rental in Big Pine Key
Island Time 1 (half of duplex), holiday rental in Big Pine Key
Island Time 1 (half of duplex), holiday rental in Big Pine Key

Island Time 1 (half of duplex)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Welcome to Casa Del Mar  ***********, holiday rental in Big Pine Key
Welcome to Casa Del Mar  ***********, holiday rental in Big Pine Key
Welcome to Casa Del Mar  ***********, holiday rental in Big Pine Key

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Family friendly canal home,150 ft dock, easy access to Atl & Gulf, holiday rental in Big Pine Key
Family friendly canal home,150 ft dock, easy access to Atl & Gulf, holiday rental in Big Pine Key
Family friendly canal home,150 ft dock, easy access to Atl & Gulf, holiday rental in Big Pine Key

Family friendly canal home,150 ft dock, easy access to Atl & Gulf

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Island Time 2 (half of duplex), holiday rental in Big Pine Key
Island Time 2 (half of duplex), holiday rental in Big Pine Key
Island Time 2 (half of duplex), holiday rental in Big Pine Key

Island Time 2 (half of duplex)

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Charming Elevated Waterfront Home, holiday rental in Big Pine Key
Charming Elevated Waterfront Home, holiday rental in Big Pine Key
Charming Elevated Waterfront Home, holiday rental in Big Pine Key

Charming Elevated Waterfront Home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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