Home Vacation Home Rentals By Owner In Big Pine Key, FL

Showing 100 Of 134 Vacation Rentals
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$336.61

/ Nightly
Private Vacation Home

Beautiful 2 Bedroom Pool Home On Big Pine Key

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$337.96

/ Nightly
Private Vacation Home

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

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(1)

$338.9

/ Nightly
Private Vacation Home

Blue Coral Lagoon Pool Seaside

Big Pine Key, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(6)

$347.83

/ Nightly
Private Vacation Home

Slice of Paradise: Big Pine Key Waterfront | Heated Pool, Dockage & Open-Water Views

Big Pine Key, Florida, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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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

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(8)

$356.69

/ Nightly
Private Vacation Home

Waterfront Oasis in the Keys

Big Pine Key, Florida, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$368.93

/ Nightly
Private Vacation Home

Pristine Waterfront Charmer - Outdoor Living & Dining, Dock, AC - Snowbirds OK

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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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

Bed 3

Bed

Bath 2

Bath

Sleep 14

Sleeps
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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

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$379.09

/ Nightly
Private Vacation Home

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

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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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

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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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

Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps
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$391.9

/ Nightly
Private Vacation Home

Sunset Hideaway, Pool home on canal

Big Pine Key, Florida, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$395.68

/ Nightly
Private Vacation Home

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

Big Pine Key, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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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

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$402.2

/ Nightly
Private Vacation Home

Recently renovated oceanfront home in Big Pine

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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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

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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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

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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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

Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps
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$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

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Home Most popular vacation rentals in Big Pine Key

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$268.79

/ Nightly
Private vacation home

Waterfront Pool Home! - Heavenly Hideout - Big Pine Key

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$247.09

/ Nightly
Private vacation home

Christmas in the FL Keys!!! Stunning sunsets, beaches 10 min away, Fishing!!!

Big Pine Key, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$249.26

/ Nightly
Private vacation home

Excellent boating location-65 ft frontage on deep canal

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$249.38

/ Nightly
Mobile home

Airstream Travel Trailer

Big Pine Key, Florida, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$251.27

/ Nightly
Private vacation home

Amazing Paradise House Canal Front with access to Atlantic and Gulf.

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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$252.54

/ Nightly
Private vacation home

Perfect getaway keys

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$262.17

/ Nightly
Private vacation home

? HEATED SWIM SPA / OPEN WATER VIEWS / BOAT DOCK / LUXURIOUS / BUILT IN 2023?

Big Pine Key, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$263.69

/ Nightly
Private vacation home

Casa Blanca | Georgeous home on Big Pine Key

Big Pine Key, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$294.95

/ Nightly
Private vacation home

Canal Front Home in Big Pine Key with Pool

BIG PINE KEY, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$290.18

/ Nightly
Private vacation home

\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"

Big Pine Key, Florida, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

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