Vacation Home Rentals By Owner In Big Pine Key, FL

Showing 40 Of 134 Vacation Rentals

Exceptional(1)

$369.9

/ Nightly

Private Vacation Home

Canal-Front Keys Retreat / Jacuzzi • Sleeps 14

Big Pine Key, Florida, United States

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Exceptional(33)

$373.22

/ Nightly

Private Vacation Home

Amazing Pool & Canal Ground Level Home, Ocean access

Big Pine Key, Florida, United States

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Bath

Sleeps

$379.09

/ Nightly

Private Vacation Home

Honey Hole a Big Pine Key paradise, canal to Bogie Channel

Big Pine Key, Florida, United States

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Exceptional(1)

$379.24

/ Nightly

Private Vacation Home

3-bedroom waterfront. Cable-WiFi, AC, Hot tub, Dock. Book for Winter 2026-27 !!

Big Pine Key, Florida, United States

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Exceptional(4)

$390.95

/ Nightly

Private Vacation Home

Modern multi story waterfront home, 30 minutes from Key west.

Big Pine Key, Florida, United States

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Bath

Sleeps

$391.9

/ Nightly

Private Vacation Home

Sunset Hideaway, Pool home on canal

Big Pine Key, Florida, United States

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Sleeps

$395.68

/ Nightly

Private Vacation Home

Spacious, Well Maintained, 3 Bedroom Canal Home on Big Pine Key

Big Pine Key, Florida, United States

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Bath

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Exceptional(2)

$396.56

/ Nightly

Private Vacation Home

POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate

Big Pine Key, Florida, United States

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$402.2

/ Nightly

Private Vacation Home

Recently renovated oceanfront home in Big Pine

Big Pine Key, Florida, United States

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Exceptional(9)

$408.29

/ Nightly

Private Vacation Home

Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!

Big Pine Key, Florida, United States

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Exceptional(1)

$408.38

/ Nightly

Private Vacation Home

Secluded Tropical Retreat: 60' Dock, Large Pool, World-Class Fishing & Lobster

Big Pine Key, Florida, United States

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Exceptional(5)

$409.31

/ Nightly

Private Vacation Home

The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE

Gordon Road, Florida, United States

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Sleeps

$411.55

/ Nightly

Private Vacation Home

A Serene Florida Escape in Big Pine Key 3 bed 2 bath house, pool, dock, sleep 6

Big Pine Key, Florida, United States

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Exceptional(5)

$429.63

/ Nightly

Private Vacation Home

Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool

Big Pine Key, Florida, United States

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Bath

Sleeps

$629.54

/ Nightly

Private Vacation Home

SEA FOREVER! Gorgeous Ocean-Front Paradise!

Big Pine Key, Florida, United States

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Exceptional(66)

$701.71

/ Nightly

Private Vacation Home

Island Sunrise Resort- 3 acre estate with open water sunrises.

Big Pine Key, Florida, United States

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Exceptional(8)

$648.49

/ Nightly

Private Vacation Home

Beautiful Open-Water Property

Big Pine Key, Florida, United States

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Exceptional(15)

$641

/ Nightly

Private Vacation Home

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Big Pine Key, Florida, United States

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Exceptional(9)

$636.58

/ Nightly

Private Vacation Home

Pool house with open water and sunset in the Florida Keys

Big Pine Key, Florida, United States

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Bath

Sleeps

$601.25

/ Nightly

Private Vacation Home

Ocean Front Beach Home on Semi Private Island Only Accessible by Boat

Cook Island, Florida, United States

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Rent a place that suits your needs

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Big Pine Key, FL

$369.9

$373.22

$379.09

$379.24

$390.95

$391.9

$395.68

$396.56

$402.2

$408.29

$408.38

$409.31

$411.55

$429.63

$629.54

$701.71

$648.49

$641

$636.58

$601.25

Rent a place that suits your needs

Most popular vacation rentals in Big Pine Key

$268.79

$247.09

$249.26

$249.38

$251.27

$252.54

$262.17

$263.69

$294.95

$290.18

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