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Big Pine Key Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
136 rentals in Big Pine Key.
Tiny Cottage in Keys 30 min from Key West, vacation rental in Big Pine Key
Tiny Cottage in Keys 30 min from Key West, vacation rental in Big Pine Key
Tiny Cottage in Keys 30 min from Key West, vacation rental in Big Pine Key

Tiny Cottage in Keys 30 min from Key West

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tropical Caribbean Wonderland, vacation rental in Big Pine Key
Tropical Caribbean Wonderland, vacation rental in Big Pine Key
Tropical Caribbean Wonderland, vacation rental in Big Pine Key

Tropical Caribbean Wonderland

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Water's Edge, vacation rental in Big Pine Key
Water's Edge, vacation rental in Big Pine Key
Water's Edge, vacation rental in Big Pine Key

Water's Edge

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tiki Beach,Bring your boat stay a week,4BR/3BA ocean front, private pool & dock, vacation rental in Big Pine Key
Tiki Beach,Bring your boat stay a week,4BR/3BA ocean front, private pool & dock, vacation rental in Big Pine Key
Tiki Beach,Bring your boat stay a week,4BR/3BA ocean front, private pool & dock, vacation rental in Big Pine Key

Tiki Beach,Bring your boat stay a week,4BR/3BA ocean front, private pool & dock

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Awesome Open Water View at Blue Heron Estate, vacation rental in Big Pine Key
Awesome Open Water View at Blue Heron Estate, vacation rental in Big Pine Key
Awesome Open Water View at Blue Heron Estate, vacation rental in Big Pine Key

Awesome Open Water View at Blue Heron Estate

Rental Home
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Charming Elevated Waterfront Home, vacation rental in Big Pine Key
Charming Elevated Waterfront Home, vacation rental in Big Pine Key
Charming Elevated Waterfront Home, vacation rental in Big Pine Key

Charming Elevated Waterfront Home

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Palmetto Retreat, vacation rental in Big Pine Key
Palmetto Retreat, vacation rental in Big Pine Key
Palmetto Retreat, vacation rental in Big Pine Key

Palmetto Retreat

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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You can see the ocean from every room in this house… look no further. ☀️, vacation rental in Big Pine Key
You can see the ocean from every room in this house… look no further. ☀️, vacation rental in Big Pine Key
You can see the ocean from every room in this house… look no further. ☀️, vacation rental in Big Pine Key

You can see the ocean from every room in this house… look no further. ☀️

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SPACIOUS RV IN THE KEYS, vacation rental in Big Pine Key
SPACIOUS RV IN THE KEYS, vacation rental in Big Pine Key
SPACIOUS RV IN THE KEYS, vacation rental in Big Pine Key

SPACIOUS RV IN THE KEYS

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sun Hutt: Serene island getaway, vacation rental in Big Pine Key
Sun Hutt: Serene island getaway, vacation rental in Big Pine Key
Sun Hutt: Serene island getaway, vacation rental in Big Pine Key

Sun Hutt: Serene island getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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You will feel like at home, vacation rental in Big Pine Key
You will feel like at home, vacation rental in Big Pine Key
You will feel like at home, vacation rental in Big Pine Key

You will feel like at home

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Adorable apartment on canal with easy boating access, vacation rental in Big Pine Key
Adorable apartment on canal with easy boating access, vacation rental in Big Pine Key
Adorable apartment on canal with easy boating access, vacation rental in Big Pine Key

Adorable apartment on canal with easy boating access

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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PARADISE IN YOUR HANDS, vacation rental in Big Pine Key
PARADISE IN YOUR HANDS, vacation rental in Big Pine Key
PARADISE IN YOUR HANDS, vacation rental in Big Pine Key

PARADISE IN YOUR HANDS

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Big Pine Key/Hot tub/Canal Home/updated, vacation rental in Big Pine Key
Big Pine Key/Hot tub/Canal Home/updated, vacation rental in Big Pine Key
Big Pine Key/Hot tub/Canal Home/updated, vacation rental in Big Pine Key

Big Pine Key/Hot tub/Canal Home/updated

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Treehouse, vacation rental in Big Pine Key
Treehouse, vacation rental in Big Pine Key
Treehouse, vacation rental in Big Pine Key

Treehouse

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel &, vacation rental in Big Pine Key
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel &, vacation rental in Big Pine Key
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel &, vacation rental in Big Pine Key

Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel &

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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You’re on island time at “The Island Girl”., vacation rental in Big Pine Key
You’re on island time at “The Island Girl”., vacation rental in Big Pine Key
You’re on island time at “The Island Girl”., vacation rental in Big Pine Key

You’re on island time at “The Island Girl”.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Banana Republics - Located in Paradise, vacation rental in Big Pine Key
Banana Republics - Located in Paradise, vacation rental in Big Pine Key
Banana Republics - Located in Paradise, vacation rental in Big Pine Key

Banana Republics - Located in Paradise

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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LARGE LOT & RV | LOWER KEYS, vacation rental in Big Pine Key
LARGE LOT & RV | LOWER KEYS, vacation rental in Big Pine Key
LARGE LOT & RV | LOWER KEYS, vacation rental in Big Pine Key

LARGE LOT & RV | LOWER KEYS

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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House 2 bedroom  2 bath Large enclosed porch overlooking canal with boat dock, vacation rental in Big Pine Key
House 2 bedroom  2 bath Large enclosed porch overlooking canal with boat dock, vacation rental in Big Pine Key
House 2 bedroom  2 bath Large enclosed porch overlooking canal with boat dock, vacation rental in Big Pine Key

House 2 bedroom 2 bath Large enclosed porch overlooking canal with boat dock

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront, bayview home with dockage, vacation rental in Big Pine Key
Waterfront, bayview home with dockage, vacation rental in Big Pine Key
Waterfront, bayview home with dockage, vacation rental in Big Pine Key

Waterfront, bayview home with dockage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Acces, vacation rental in Big Pine Key
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Acces, vacation rental in Big Pine Key
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Acces, vacation rental in Big Pine Key

Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Acces

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Yellowstone by the Sea, vacation rental in Big Pine Key
Yellowstone by the Sea, vacation rental in Big Pine Key
Yellowstone by the Sea, vacation rental in Big Pine Key

Yellowstone by the Sea

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Prime Time 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel, vacation rental in Big Pine Key
Prime Time 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel, vacation rental in Big Pine Key
Prime Time 2 - Charming Canal Front Duplex, Quick Trip To South Pine Channel, vacation rental in Big Pine Key

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Relaxing canal front home in nature preserve, vacation rental in Big Pine Key
Relaxing canal front home in nature preserve, vacation rental in Big Pine Key
Relaxing canal front home in nature preserve, vacation rental in Big Pine Key

Relaxing canal front home in nature preserve

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key
New Listing! Beautiful Canal front , Key Deer and jacuzzi., vacation rental in Big Pine Key

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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PARADISE IN YOUR HANDS, vacation rental in Big Pine Key
PARADISE IN YOUR HANDS, vacation rental in Big Pine Key
PARADISE IN YOUR HANDS, vacation rental in Big Pine Key

PARADISE IN YOUR HANDS

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fisherman's Paradise in the Heart of Big Pine Key , vacation rental in Big Pine Key
Fisherman's Paradise in the Heart of Big Pine Key , vacation rental in Big Pine Key
Fisherman's Paradise in the Heart of Big Pine Key , vacation rental in Big Pine Key

Fisherman's Paradise in the Heart of Big Pine Key

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Remodeled Corner House on the Water, vacation rental in Big Pine Key
Newly Remodeled Corner House on the Water, vacation rental in Big Pine Key
Newly Remodeled Corner House on the Water, vacation rental in Big Pine Key

Newly Remodeled Corner House on the Water

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, vacation rental in Big Pine Key
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, vacation rental in Big Pine Key
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm, vacation rental in Big Pine Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, vacation rental in Big Pine Key
2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, vacation rental in Big Pine Key
2/2 Canal Front Home Big Pine Key.  Easy ocean and gulf access!, vacation rental in Big Pine Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Boaters Dream House in the Water with 175’ of Sea Wall, vacation rental in Big Pine Key
Boaters Dream House in the Water with 175’ of Sea Wall, vacation rental in Big Pine Key
Boaters Dream House in the Water with 175’ of Sea Wall, vacation rental in Big Pine Key

Boaters Dream House in the Water with 175’ of Sea Wall

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Escape to Eden: Cute canalfront getaway with boating, vacation rental in Big Pine Key
Escape to Eden: Cute canalfront getaway with boating, vacation rental in Big Pine Key
Escape to Eden: Cute canalfront getaway with boating, vacation rental in Big Pine Key

Escape to Eden: Cute canalfront getaway with boating

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Boater’s Dream House 3 bedroom 2 bath with 200’ of Dock Space, vacation rental in Big Pine Key
Boater’s Dream House 3 bedroom 2 bath with 200’ of Dock Space, vacation rental in Big Pine Key
Boater’s Dream House 3 bedroom 2 bath with 200’ of Dock Space, vacation rental in Big Pine Key

Boater’s Dream House 3 bedroom 2 bath with 200’ of Dock Space

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friend, vacation rental in Big Pine Key
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friend, vacation rental in Big Pine Key
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friend, vacation rental in Big Pine Key

Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friend

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bungalow oasis with lots of room, vacation rental in Big Pine Key
Bungalow oasis with lots of room, vacation rental in Big Pine Key
Bungalow oasis with lots of room, vacation rental in Big Pine Key

Bungalow oasis with lots of room

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Canal Front Home in Big Pine Key, vacation rental in Big Pine Key
Canal Front Home in Big Pine Key, vacation rental in Big Pine Key
Canal Front Home in Big Pine Key, vacation rental in Big Pine Key

Canal Front Home in Big Pine Key

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve, vacation rental in Big Pine Key
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve, vacation rental in Big Pine Key
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve, vacation rental in Big Pine Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cedar Cottage: Cute boating home, vacation rental in Big Pine Key
Cedar Cottage: Cute boating home, vacation rental in Big Pine Key
Cedar Cottage: Cute boating home, vacation rental in Big Pine Key

Cedar Cottage: Cute boating home

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tarpon Tales: Fantastic boating on Big Pine Key, vacation rental in Big Pine Key
Tarpon Tales: Fantastic boating on Big Pine Key, vacation rental in Big Pine Key
Tarpon Tales: Fantastic boating on Big Pine Key, vacation rental in Big Pine Key

Tarpon Tales: Fantastic boating on Big Pine Key

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Canal Front Paradise!, vacation rental in Big Pine Key
Canal Front Paradise!, vacation rental in Big Pine Key
Canal Front Paradise!, vacation rental in Big Pine Key

Canal Front Paradise!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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FISHERMANS DREAM HOUSE, vacation rental in Big Pine Key
FISHERMANS DREAM HOUSE, vacation rental in Big Pine Key
FISHERMANS DREAM HOUSE, vacation rental in Big Pine Key

FISHERMANS DREAM HOUSE

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Paradise Found !  Fully updated Waterfront Home- GREAT FISHING, vacation rental in Big Pine Key
Paradise Found !  Fully updated Waterfront Home- GREAT FISHING, vacation rental in Big Pine Key
Paradise Found !  Fully updated Waterfront Home- GREAT FISHING, vacation rental in Big Pine Key

Paradise Found ! Fully updated Waterfront Home- GREAT FISHING

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Family Big Pine Retreat! Short drive to Key West!, vacation rental in Big Pine Key
Beautiful Family Big Pine Retreat! Short drive to Key West!, vacation rental in Big Pine Key
Beautiful Family Big Pine Retreat! Short drive to Key West!, vacation rental in Big Pine Key

Beautiful Family Big Pine Retreat! Short drive to Key West!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key
Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access, vacation rental in Big Pine Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CASA COCO BY THE CANAL!!!, vacation rental in Big Pine Key
CASA COCO BY THE CANAL!!!, vacation rental in Big Pine Key
CASA COCO BY THE CANAL!!!, vacation rental in Big Pine Key

CASA COCO BY THE CANAL!!!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Tropical Canal-front Cottage in the Lower Florida Keys, vacation rental in Big Pine Key
Tropical Canal-front Cottage in the Lower Florida Keys, vacation rental in Big Pine Key
Tropical Canal-front Cottage in the Lower Florida Keys, vacation rental in Big Pine Key

Tropical Canal-front Cottage in the Lower Florida Keys

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Reel Paradise on Big Pine Key, vacation rental in Big Pine Key
Reel Paradise on Big Pine Key, vacation rental in Big Pine Key
Reel Paradise on Big Pine Key, vacation rental in Big Pine Key

Reel Paradise on Big Pine Key

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private water front property with ocean access, vacation rental in Big Pine Key
Private water front property with ocean access, vacation rental in Big Pine Key
Private water front property with ocean access, vacation rental in Big Pine Key

Private water front property with ocean access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Fill the Day with Sun & Fun!, vacation rental in Big Pine Key
Fill the Day with Sun & Fun!, vacation rental in Big Pine Key
Fill the Day with Sun & Fun!, vacation rental in Big Pine Key

Fill the Day with Sun & Fun!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-50 of 136
Frequently Asked Questions about Big Pine Key






Big Pine Key Vacation Rental
Big Pine Key and its neighboring islands are some of the most popular vacation destinations for families who want to rent a beachfront house or condo. The climate in this part of Florida is delightful and very similar to the warm and pleasant climates of the Caribbean. The crystal blue waters and the white sandy beaches in Big Pine Key make this an impressive location for your next vacation rental.
Things to Do
Big Pine Key is a fantastic place to come if you want to get away from all the troubles and stress of day-to-day life. The vacation houses and condos available here are designed for rest and relaxation. The main appeal of Big Pine Key is the tranquil environment and beautiful scenery. There are plenty of outdoor activities that you can enjoy when you’re not in your rental home, such as fishing, walking and biking, and seeking out wildlife.
Family Fun
If you’re visiting Big Pine Key with children, there are numerous wonderful activities that will get them out of the rental home for the day. The Theater of the Sea and the National Key Deer Refuge are great options for the whole family. If you would like to spot some of the many alligators that reside in the area, then you should head to the Blue Hole.
Delicious Dining in Big Pine Key
If you’re staying in a vacation home in Big Pine Key, you may choose to dine in and enjoy a quiet intimate or pizza with the family. There are many local groceries where you can purchase fresh seafood and produce to prepare a meal in your condo or villa. However, if you do fancy a meal out, you can take a trip to Rob’s Island Grill, The Big Pine Restaurant, or The China Garden. All of these restaurants are local and provide culinary delights.
Benefits of Big Pine Key Rentals
Unlike a hotel, staying in a Big Pine Key vacation rental provides you with complete privacy and tranquility during your vacation. Enjoy the space and security you can get from your own beautiful rental home.