Vacation Rentals By Owner In Big Pine Key, FL

Showing 20 Of 145 Vacation Rentals

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(4)

$314.51

/ Nightly

Private Vacation Home

Easy access to beautiful Keys water & a short drive to Key West fun!

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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Exceptional(2)

$561.96

/ Nightly

Private Vacation Home

Open 360 water view, boat dockage, 4 bedroom Home in Big Pine Key

Big Pine Key, Florida, United States

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$196.84

/ Nightly

Private Vacation Home

Secluded Hideaway with private pool and canal

Big Pine Key, Florida, United States

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Sleeps

$337.96

/ Nightly

Private Vacation Home

Beautifully updated on water, near Bahia Honda Beach, Key Deer preserve

Big Pine Key, Florida, United States

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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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Sleeps

$237.36

/ Nightly

Private Vacation Home

Hidden Keys Paradise-Where the Key Deer Roam-75’ Private Dock! Boaters Paradise!

Big Pine Key, Florida, United States

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$219.71

/ Nightly

Private Vacation Home

Escape to Eden | Sunset Views & Dockage

Big Pine Key, Florida, United States

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Exceptional(80)

Select Dates for Price

Private Vacation Home

Big Pine - Bring your boat! - 4BR/3BA ocean front, private pool & dock

Big Pine Key, Florida, United States

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$1104.79

/ Nightly

Private Vacation Home

Private Island Beach house Charming 3-bedroom - The true privilege of seclusion

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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$153.93

/ Nightly

Private Vacation Home

Captain & Mermaid's Diamond #BP25

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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Exceptional(3)

$186.55

/ Nightly

Private Vacation Home

Boater's Paradise with Boat Dock / Quick Open Water Access

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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Sleeps

$211.37

/ Nightly

Private Vacation Home

Reel Paradise | Boating & fabulous sunsets

Big Pine Key, Florida, United States

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Exceptional(5)

$354.44

/ Nightly

Private Vacation Home

Big Pine Paradise: Beautiful Updated 4BR Canal Front Home, Pool, Dockage, Easy Gulf/Atlantic Access

Big Pine Key, Florida, United States

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$218.82

/ Nightly

Private Vacation Home

Private Pool • Tropical Oasis • Minutes to Bahia Honda

Big Pine Key, Florida, United States

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$223.13

/ Nightly

Private Vacation Home

4-bedroom house canal front home in beautiful Big Pine Key

Big Pine Key, Florida, United States

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Rent a place that suits your needs

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Vacation Rentals By Owner In Big Pine Key, FL

$408.29

$314.51

$390.95

$561.96

$196.84

$337.96

$369.9

$237.36

$219.71

$1104.79

$379.24

$153.93

$636.58

$186.55

$641

$211.37

$354.44

$218.82

$223.13

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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