Vacation Rentals in Big Pine Key, Florida

49 Properties Available

Boat dockage & a great Gulf-front Big Pine retreat Private vacation home
Boat dockage & a great Gulf-front Big Pine retreat
$1050 / night
View Details
Awesome Open Water View at Blue Heron Estate Private vacation home
Awesome Open Water View at Blue Heron Estate
$968 / night
View Details
Exclusive 5BR Oasis: Private Pool, Hot Tub, Lush Gardens, Canal Views & Privacy. Private vacation home
Exclusive 5BR Oasis: Private Pool, Hot Tub, Lush Gardens, Canal Views & Privacy.
$675 / night
View Details
Charming 3-bedroom house in Big Pine Key near Beach and Key West Private vacation home
Charming 3-bedroom house in Big Pine Key near Beach and Key West
$599 / night
View Details
Pool house with open water and sunset in the Florida Keys Private vacation home
Pool house with open water and sunset in the Florida Keys
$570 / night
View Details
Beach View Room Barnacle bed and breakfast Bed & breakfast
Beach View Room Barnacle bed and breakfast
$522 / night
View Details
Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit. Dogs OK Private vacation home
Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit. Dogs OK
$517 / night
View Details
Beautiful Family Big Pine Retreat! Short drive to Key West! Bed & breakfast
Beautiful Family Big Pine Retreat! Short drive to Key West!
$513 / night
View Details
Big Pine Latitude Adjustment Private vacation home
Big Pine Latitude Adjustment
$501 / night
View Details
Gorgeous Beachfront Home with a pool. Water views from every direction. Private vacation home
Gorgeous Beachfront Home with a pool. Water views from every direction.
$490 / night
View Details
Island Sunrise Resort- 3 acre estate with open water sunrises. Private vacation home
Island Sunrise Resort- 3 acre estate with open water sunrises.
$485 / night
View Details
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate Private vacation home
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
$463 / night
View Details
Sunset Hideaway, Pool home on canal Private vacation home
Sunset Hideaway, Pool home on canal
$396 / night
View Details
Waterfront Oasis in the Keys Private vacation home
Waterfront Oasis in the Keys
$352 / night
View Details
Beautiful 2 Bedroom Pool Home On Big Pine Key Private vacation home
Beautiful 2 Bedroom Pool Home On Big Pine Key
$327 / night
View Details
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW Private vacation home
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
$307 / night
View Details
Keys 3 Bedroom Corner Home near Beach & Key West Private vacation home
Keys 3 Bedroom Corner Home near Beach & Key West
$299 / night
View Details
Boater’s Paradise: 3BR Canal Front Home + Fish Cleaning Station Private vacation home
Boater’s Paradise: 3BR Canal Front Home + Fish Cleaning Station
$286 / night
View Details
4\/2 Fully Furnished Canal Home Private vacation home
4\/2 Fully Furnished Canal Home
$275 / night
View Details
Newly Renovated Boater’s Paradise -35' Dock + Ice • No Low Bridges Private vacation home
Newly Renovated Boater’s Paradise -35' Dock + Ice • No Low Bridges
$274 / night
View Details
Seahorse Sunset Cottage is your destination retreat in Big Pine Key! Private vacation home
Seahorse Sunset Cottage is your destination retreat in Big Pine Key!
$269 / night
View Details
Waterfront Pool Home! - Heavenly Hideout - Big Pine Key Private vacation home
Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
$263 / night
View Details
New listing 3bd\/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key Private vacation home
New listing 3bd\/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
$263 / night
View Details
Big Pine Retreat will leave you wanting to come back year after year! Private vacation home
Big Pine Retreat will leave you wanting to come back year after year!
$263 / night
View Details
Ocean views from every room. This peaceful and gorgeous property has a NEW DOCK! Private vacation home
Ocean views from every room. This peaceful and gorgeous property has a NEW DOCK!
$256 / night
View Details
Perfect getaway keys Private vacation home
Perfect getaway keys
$252 / night
View Details
Yellowstone by the Sea Private vacation home
Yellowstone by the Sea
$244 / night
View Details
Big Pine Getaway - Pets + Boats Welcome Private vacation home
Big Pine Getaway - Pets + Boats Welcome
$244 / night
View Details
Escape to Eden | Sunset Views & Dockage Private vacation home
Escape to Eden | Sunset Views & Dockage
$234 / night
View Details
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations! Private vacation home
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations!
$225 / night
View Details
Escape to Paradise, a 3-bedroom canal home on Big Pine Key. Private vacation home
Escape to Paradise, a 3-bedroom canal home on Big Pine Key.
$220 / night
View Details
Newly Remodeled Corner House on the Water Private vacation home
Newly Remodeled Corner House on the Water
$219 / night
View Details
Easy access to beautiful Keys water & a short drive to Key West fun! Private vacation home
Easy access to beautiful Keys water & a short drive to Key West fun!
$219 / night
View Details
Peaceful island home on canal with quick access to Bogie Channel. Private vacation home
Peaceful island home on canal with quick access to Bogie Channel.
$214 / night
View Details
Private Pool • Tropical Oasis • Minutes to Bahia Honda Private vacation home
Private Pool • Tropical Oasis • Minutes to Bahia Honda
$214 / night
View Details
Reel Paradise | Fabulous sunsets from this canalfront 2 bed\/2 bath on Big Pine Key Private vacation home
Reel Paradise | Fabulous sunsets from this canalfront 2 bed\/2 bath on Big Pine Key
$209 / night
View Details
Big Pine Key Home on Bogie Channel w\/ Dock & Slip! Private vacation home
Big Pine Key Home on Bogie Channel w\/ Dock & Slip!
$203 / night
View Details
Canal Front Home With Pool And Hot Tub Private vacation home
Canal Front Home With Pool And Hot Tub
$203 / night
View Details
Canal Front Paradise! Just a few yards from open water! Private vacation home
Canal Front Paradise! Just a few yards from open water!
$190 / night
View Details
Tiki Breeze | Canalfront getaway in the heart of Big Pine Key Private vacation home
Tiki Breeze | Canalfront getaway in the heart of Big Pine Key
$179 / night
View Details
Boater's Paradise with Boat Dock \/ Quick Open Water Access Private vacation home
Boater's Paradise with Boat Dock \/ Quick Open Water Access
$175 / night
View Details
Relaxing Florida Keys canal front home in nature preserve Private vacation home
Relaxing Florida Keys canal front home in nature preserve
$160 / night
View Details
Secluded Hideaway- pivate pool and boat dockage Private vacation home
Secluded Hideaway- pivate pool and boat dockage
$154 / night
View Details
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve Private vacation home
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve
$133 / night
View Details
Palm Grove Paradise - Private Garden Oasis on Big Pine Key 2\/1.5 Mobile home
Palm Grove Paradise - Private Garden Oasis on Big Pine Key 2\/1.5
$121 / night
View Details
Easy access to the Ocean and Gulf Private vacation home
Easy access to the Ocean and Gulf
$0 / night
View Details
Fill the Day with Sun & Fun! Private vacation home
Fill the Day with Sun & Fun!
$0 / night
View Details
LARGE LOT & RV | LOWER KEYS Caravan Park/Campsite
LARGE LOT & RV | LOWER KEYS
$0 / night
View Details
PARADISE IN YOUR HANDS Private vacation home
PARADISE IN YOUR HANDS
$0 / night
View Details