Big Pine Key Vacation Rentals in the Florida Keys
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We have many choices for Big Pine Key Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer for your visit to Florida.
Canal Front Paradise! Just a few yards from open water!
Big Pine Key Private vacation home 
10.0
Welcome to paradise! Want to live like a local? Fish the reefs, snorkel Looe Key, dive for lobster, or kayak to the open water of Big Pine Channel, where dolphin and manatee play. Then return to your denizen and watch the boats turn for home. Relax on the porch, as the key deer meander out of the thickets in the early evening. Watch as a spectacula.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 8
Island Sunrise Resort- 3 acre estate with open water sunrises.
big pine key Private vacation home 10.0
Island Sunrise Resort is a 3 acre open water estate. Enjoy the 250' dock, pool, spectacular views of distant islands and the Old Bahia Honda railroad bridge during your stay at your own mini-resort. The Coral House (31463 featured house sleeps 8+) has a split floor plan with an eat-in kitchen and formal dining room. There is an additional 3/2 home,.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Canal Front Home With Pool And Hot Tub
Big Pine Key Private vacation home 10.0
Terrific tropical getaway for rent!! 2 Bedroom 3 full bath canal front home with large in ground pool, hot tub and 60 feet of dock age! Located in desirable Doctor's Arm neighborhood, this house is located just steps from the famous No Name Pub on Big Pine Key. The boating cannel is just 200 yards to open water onto Bogie Channel and Spanish Har.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
Manatee Watch | 5 bedrooms, pool, ocean access
Big Pine Key Private vacation home 10.0
Updated 5-bedroom, 3-bathroom boating home just four houses in from Pine Channel on the oceanside of Big Pine Key with gorgeous custom pool & spa. 60-foot concrete dock with large fender piles for your big boat. Convenient steps down into the deep water 70-foot wide canal so you can go for a swim or launch a kayak or paddleboard. Clear, deep cana.......read more
5 Bedroom(s)
3 Bath(s) Sleeps 12
Lower Keys Retreat..... Come.... Relax in Paradise!!
Big Pine Key Private vacation home 9.8
This beautiful home located in Eden Pines subdivision on Big Pine Key has the best of everything. Furnished with the finest tropical decor, flat screen TV's, wireless internet and roomy kitchen. Quiet setting, with landscaped yard & Heated Pool
The large living area is spacious and cheery with tall cathedral ceilings. The kitchen is perfect .......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Paradise Retreat ~ BPK
Big Pine Key Private vacation home 10.0
~3/2 home with heated pool located on large ,private and fenced property. Screened room and patio deck. Privacy is key to relaxation here on this property in Big Pine Key.
~Boat ramp within 1/4 mile with excellent access to Gulf~Atlantic
~Quick 20 minutes to our favorite "Square Grouper Restaurant", 45 minutes to Key West and 25 minutes to M.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
Big Pine Key Private vacation home 10.0
This cozy, clean, canal front home is located in a quiet, family friendly, National Key Deer Refuge. 3 bedroom, 2 baths with screened in porch, and plenty of outdoor living area underneath. Master bedroom with king bed with attached bathroom. One guest bedroom with queen bed, and the other with 2 twins, 2nd bathroom conveniently located inbetween........read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Awesome Open Water View at Blue Heron Estate
Big Pine Key Private vacation home 10.0
15 Acre Open Water Estate. Four bedrooms each with their own private bathroom. Large pool. Breathtaking views of the sunrise and historic Bahia Honda Bridge. Secluded location at the end of the road. Less than 2 miles to the Atlantic and around 3 miles to the Back Country. Check out the satellite view of the property and see for yourself. No doubt.......read more
4 Bedroom(s)
5 Bath(s) Sleeps 9
2/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!
Big Pine Key Private vacation home 9.6
Terrific Key getaway for rent!! Newly remodeled 2 Bedroom 2 full bath canal front home with 50 feet of dock. Located in desirable Doctor's Arm neighborhood, this house is just around the corner from the famous No Name Pub on Big Pine Key. Quick idle to Spanish Harbor Channel and easy access to the ocean or the gulf. Less than a mile from the No .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
Big Pine Key Private vacation home 8.8
Florida Keys, Big Pine Key, located in Big Pine Key Florida. This home was remodeled in 2018 with new everything including a new AC unit. It's on a private canal on the bay side on Big Pine Key, in The Florida Keys, not far from Key West or Marathon Florida, close to shopping and still very private. Bring your boat there's plenty of dock space. Boa.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 6
\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
Big Pine Key Private vacation home 10.0
-Remodeling house 3 bedroom and 3 bath.
-Please note that there is a 28 minimum rental period for this property.
- Dock and fish cleaning station.
-Excellent access to Atlantic and Gulf, minutes to the best lower keys fishing in country.
-Nice Jacuzzi to enjoy the sunset.
- 15 minutes from Bahia Honda State Park with a beautiful.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm
Big Pine Key Private vacation home 9.4
The property has direct access to the Atlantic Ocean or the Gulf in minutes, providing some of the finest bluewater fishing coupled with backwater bonefish and permit fishing rivaled to none. The Looe Key National Park, famous for it's crystal clear water, brilliant tropical fish and live coral is only 4 miles off Big PIne Key, great for diving or.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
Big Pine Key Private vacation home 10.0
Please note that we have a 28 day minimum rental period with no subletting. This is a Monroe County Regulation to preserve the beauty and peacefulness of Big Pine Key. PLEASE CLICK VIEW MORE BELOW TO VIEW CANCELLATION POLICY
My property is a rare find in the lower keys. Nestled in the middle of the Key Deer Wildlife Refuge. This house is.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
Big Pine Key Private vacation home 10.0
Searching for your own private Keys resort?
Look no further! Our "Retiro Sin Nombre" home is located on the famed and remote No Name Key.
This home offers a wonderful opportunity to enjoy the many nearby water sports, including abundant fishing and lobstering, diving, boating, kayaking and all the other outdoor activities in the beau.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
SEA EVERYWHERE! Open Water & 2 Boat Basins!
Big Pine Key Private vacation home
Beautiful open-water views of the Bahia Honda bridge from nearly every room!
Key deer grazing daily in your yard.
Two boat basins capable of holding boats up to 30'.
Sunrises from your living room, sunsets from your dock.
Catch tarpon and snapper right off of the dock.
10 miles to Content Key. 3 miles to Spanish Harbor.
.......read more
4 Bedroom(s)
2 Bath(s) Sleeps 9
SEA FOREVER! Gorgeous Ocean-Front Paradise!
Big Pine Key Private vacation home
This feels like your own private resort. Two tiki huts cover lounge chairs and a 13-foot shuffleboard court. The pool and 24 palm trees frame the endless ocean views. Drive your boat straight out from the house to the #1 reef in North America! The Atlantic is 3 miles from your door. Enjoy the 1,500 Key Deer on the island, which will come right up t.......read more
5 Bedroom(s)
4 Bath(s) Sleeps 12
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
Big Pine Key Private vacation home 10.0
Beautiful, newly redone home directly on the water, perfect for boating with easy access to Atlantic or Gulf. Canalside docking for your boat. Amazing sunrises on the private porch deck. New furniture. This home offers a wonderful opportunity for relaxation & enjoyment of many water sports and activities in the beautiful, tropical FL Keys. Kayaks,.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
Big Pine Key Private vacation home 10.0
Absolutely stunning, OCEANFRONT, dream home with panoramic views like none other. Truly one-of-a-kind property. BRAND NEW POOL just completed.
This brand new, beautiful 4 bedroom, 3.5 bath OCEANFRONT home is situated on a 3+ acre private peninsula in Big Pine Key offering 2,500+ square feet of spacious, new living space, plus an additional 8.......read more
4 Bedroom(s)
4 Bath(s) Sleeps 10
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations!
Big Pine Key Private vacation home 10.0
Discover the epitome of Keys living at "Rising Sun," a captivating waterfront home nestled on the serene shores of Big Pine Key. This charming abode offers an authentic experience of the vibrant Keys Life, immersing you in the essence of island living. With a private boat dock along the seawall, you can effortlessly moor your vessel and embark on a.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 8
Discounted July- ocean-ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
Big Pine Key Private vacation home 10.0
You have found it. So quiet. So beautiful. On Bogie Channel. One mile from No Name Pub. Only 30 miles from Key West! FUN IS EVERYWHERE. With ocean views from EVERY room in the home, this unique property boasts two completely separate units with an amazing one-bedroom, one-bath, and full kitchen, living, and dining area upstairs and a two-bedroom u.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Gorgeous Beachfront Home with a pool. Water views from every direction.
Big Pine Key Private vacation home 10.0
Do you want to feel like you are on your own private piece of paradise? Welcome to this 5 bedroom 3 bath home. Featuring a massive private beach with a heated pool. Plenty of privacy to relax wherever you at the home. Whether you are poolside enjoying the view, on one of three screened porches, or anywhere in the home, there is a water view. Go kay.......read more
5 Bedroom(s)
3 Bath(s) Sleeps 10
Dates available Oct, Nov, Dec 2023
Big Pine Key Private vacation home 10.0
2/2Come and enjoy this newly renovated home. Be the first to enjoy! Located in one of the best fishing spots in the Florida keys, this canal home features a ramp for your small boat or jet ski. Relax among the Key Deer, enjoy the hot tub and fire pits. The home has a large covered patio and large covered fishing station. Washer and dryer in the gar.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 7
Private water front property with ocean access
Big Pine Key Private vacation home 10.0
Beautiful 15,000 sq ft water front property.
Steps away from the famous No Name Pub.
Steps away from the no name bridge which is great for fishing.
Also in walking distance from boat rentals and kayak rentals although we have kayaks to use at our place during your stay.
30 minutes from key west and 10 minutes to the beautiful beache.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 10
Upscale ocean front home & easy canal boat access to Gulf or Atlantic
Big Pine Key Private vacation home 9.0
THE ADVENTURER'S RETREAT - BIG PINE KEY BUNGALOW IS YOUR HOME AWAY FROM HOME WHERE YOU CAN RELAX AND ENJOY THE CENTRALIZED LOCATION TO ALL THE BEST ADVENTURES THE FLORIDA KEYS HAVE TO OFFER. ALL ROOMS HAVE AN OCEAN AND/OR CANAL VIEW!
-Location-
The Big Pine Key Bungalow is located on the East side of Big Pine Key. The living room and kit.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
House 2 bedroom 2 bath Large enclosed porch overlooking canal with boat dock
Big Pine Key Private vacation home
2 bedroom 2 bath stilt home with large screened in porch overlooking canal and lush tropical coconut palms. Boat dock Within 30 minutes of Key west. 20 minute boat ride to world class reef diving and snorkeling........read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Excellent boating location-65 ft frontage on deep canal
Big Pine Key Private vacation home 10.0
Excellent location 2 bedroom 2 bath home with a 65 ft sea wall on wide canal in Big Pine Key. This is a perfect location for boaters. A marina with fuel docks is located at the end of the canal. Hopefully you won’t need it, but Boat U.S. is across the canal. The canal is the very easy to navigate and less than a 5 minute cruise to the channel. A .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
BRILLIANT VIEWS OF OPEN WATERS- 75' DOCK - 250 ' TO OPEN CHANNEL BIG PINE KEY FL
Big Pine Key Private vacation home 10.0
Welcome to our new spacious 3 bedroom 2 full bath home on a wide deep water canal with a 75 foot dock only 250 feet from the peaceful open waters of Pine Channel. The dock is equipped with a ladder and ample fenders and cleats to secure your boat. Our home is thoroughly cleaned and sanitized before each visit. Our comfortable 10 ft by 20 ft rear d.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Beautiful Family Big Pine Retreat! Short drive to Key West!
Big Pine Key Bed & breakfast
Big Pine Key offers the most peace & tranquility of the FL Keys! This home offers plenty of space and parking along side with waterfront dockage space. A private jacuzzi and a wonderful open-layout home perfect for entertaining. You have plenty of space to enjoy an amazing time with your guest. Next time your thinking of disconnecting from city lif.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Big Pine Getaway - Pets + Boats Welcome
Big Pine Key Private vacation home 10.0
Brand new! Pet friendly, quiet and clean beach house. located on Big Pine Key. Only minutes from boat ramps and white sand turquoise beaches at Bahia Honda State Park. Plenty of tiki bars within close proximity, or if you like to cook, the new kitchen is equipped with all brand new utensils and an oversized stainless-steel fridge. The home offers a.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Florida Keys Water Front Vacation Home with Pool
Big Pine Key Private vacation home
Beautiful 3-BR waterfront house with pool that is located directly on an ocean canal with easy access to the Gulf of Mexico or Atlantic Ocean. Private outside shower. 75-ft dock for boat. Home of the Key Deer and Blue Hole (the deer walk past house daily).
After a day on the ocean, sit in backyard under the tiki hut with a cold drink and gr.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters
Big Pine Key Private vacation home 9.4
Welcome to Prime Time 2 – Your Charming Waterfront Getaway on Big Pine Key! This delightful waterfront duplex on Big Pine Key offers the perfect setting for quick and easy access to open waters, setting the stage for a relaxing and adventure-filled environment. With ample seawall space, docking your boat is a breeze, and it's just a short ride to.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 6
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
Big Pine Key Private vacation home 8.0
Discover Prime Time – Your Tropical Canal Front Retreat on Big Pine Key! This delightful canal front duplex brings the essence of the Florida Keys to life, offering a vibrant tropical ambiance and direct access to open waters. Dock your boat along the seawall and set off on fantastic fishing adventures just minutes away. Start your day on the scr.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Escape the Ordinary and Experience Island Paradise
Big Pine Key Private vacation home 10.0
Tarpon Retreat is a luxurious vacation rental home, nestled in an island paradise located in the Big Pine Key Deer Refuge. This vacation rental home is the perfect destination for a peaceful and secluded getaway. Key Deer roam freely on the property and it is located in a quiet neighborhood with easy access to the Gulf of Mexico and Atlantic Ocean........read more
2 Bedroom(s)
2 Bath(s) Sleeps 8
Tropical Canal-front Cottage in the Lower Florida Keys
Big Pine Key Private vacation home
Snapper Villa is the perfect destination for those looking for a tropical getaway. Set on a canal-front in the Big Pine Key Deer Refuge, the cottage offers open water access to the Gulf of Mexico and Atlantic Ocean. Enjoy ultimate privacy in a quiet neighborhood while being surrounded by nature and all of its beauty. Steps away from the famous No N.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 8
Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home
Big Pine Key Private vacation home
Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home. Sunrise Retreat has gorgeous, unobstructed views of the ocean. There's a L shaped
floating dock that can host a 24' boat, or you can launch the provided kayaks onsite. The master bedroom has a king bed, a working desk station, balcony access, and a private bath. There is a .......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly!
Big Pine Key Private vacation home 9.2
Escape to 'Slice of Paradise' – a tropical waterfront haven nestled on the picturesque Big Pine Key. This stunning retreat showcases awe-inspiring open water views and provides a generous 60 feet of canal seawall, ensuring a perfect docking spot for your boat. With swift access to both the Atlantic and Gulf waters, you're perfectly positioned to .......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8