Big Pine Key Vacation Rentals, Cottages & Private Rental Homes.
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Vacation Rentals by Owner in Big Pine Key Florida -- We have partnered directly with a major provider for By Owner Rentals, and now have the selection and value to offer our visitors searching for places to rent in Florida. Choose from Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your stay enjoyable.
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Canal Front Paradise! Just a few yards from open water!
Private Vacation Home in Big Pine Key
Welcome to paradise! Want to live like a local? Fish the reefs, snorkel Looe Key, dive for lobster, or kayak where dolphin and manatee play. Just navigate the few hundred feet of the canal to the open water of Pine Channel.
The house is itself is fully furnished with all the amenities. Central AC, ceiling fans throughout, dishwasher, washer/dryer, range, microwave, toaster, fridge, various coffee makers.
There is plenty of room for a boat trailer or RV in a side lot adjacent to t.......
10.0 Star Review Island Sunrise Resort- 3 acre estate with open water sunrises.
Private Vacation Home in big pine key
Island Sunrise Resort is a 3 acre open water estate. Enjoy the 250' long 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, The Sand Dollar House (sleeps 6). Large groups may rent the second house also. Keep in mind, if only one house is rented, the second one will re.......
Canal Front Home With Pool And Hot Tub
Private Vacation Home in Big Pine Key
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 Harbor Channel. Less than a mile from the No Name Bridge, so there is access to fantastic fishing within walking distance even if you don't have a boat!.......
Manatee Watch | 5 bedrooms, pool, ocean access
Private Vacation Home in Big Pine Key
Summary:
Gorgeous pool, big dock & easy ocean access from this 5 bed/4 bath home on Big Pine Key
The Space:
Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offers unparalleled luxury and convenience, just seconds away from Pine Channel on the oceanside of Big Pine Key.
Nestled just four houses in from Pine Channel, this stunning property features a breathtaking custom pool and spa, perf.......
Lower Keys Retreat..... Come.... Relax in Paradise!!
Private Vacation Home in Big Pine Key
This beautiful home located in Eden Pines, a Peaceful 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 and Chilled Pool, Newly remodeled bedrooms with new furniture...
A/C system updated... quiet comfortable..
The large living area is spacious and cheery with tall cathedral ceilings. The kitchen is perfect for the group to gather for imp.......
Paradise Retreat ~ BPK
Private Vacation Home in Big Pine Key
~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 Marathon and other favorite "Burdines"
~Beautiful Winn Dixie grocery store on BPK
~28 day minimum rental for this property.......
Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
Private Vacation Home in Big Pine Key
Cozy, clean, canal front home 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. Fully equipped kitchen with attached washer/dryer combo. Dining area (seating for 6) additional table for 4 on screened in porch. Additional amenities inclu.......
Awesome Open Water View at Blue Heron Estate
Private Vacation Home in Big Pine Key
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, it is one of the best boating locations in the Lower Keys. With a 100' long dock adjacent to the property. Affordable pricing. The Blue Heron Estat.......
2/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!
Private Vacation Home in Big Pine Key
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 Name Bridge, so there is access to fantastic fishing within walking distance even if you don't have a boat!! The house is a short drive to Bahia Hond.......
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
Private Vacation Home in Big Pine Key
**** THE HOUSE IS NOW PAINTED WHITE, HAS A NEW FRESH LOOK**** 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. Boat Rental Available in town. We are looking for a seasonal renter but also consider month.......
\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
Private Vacation Home in Big Pine Key
-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.
-. Bahia Honda State Park with a beautiful beach.
-The Key where the deer live .
-Tiki bar to relax watching the canal.
-Full kitchen
-TV in every room.
-Directv and internet provider.......
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm
Private Vacation Home in Big Pine Key
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 snorkeling. The dock provides safe, secure and quick access to your boat. Launch or rent a boat at the 'No Name Bridge' and park it in the canal be.......
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
Private Vacation Home in Big Pine Key
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 located 30 miles northeast of Key West. The property consists of three full lots at the tip of Doctor's Arm Peninsula. Please take a look at the aeri.......
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
Private Vacation Home in Big Pine Key
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 beautiful tropical Florida Keys.
Peacefully rest each day in a spacious home with beautiful open living/dining room, vaulted ceiling, a large scree.......
SEA EVERYWHERE! Open Water & 2 Boat Basins!
Private Vacation Home in Big Pine Key
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.
You are in the MIDDLE of the best place to catch tarpon, lobster, mahi, mutton, hogfish, mangrove, yellowtail, sailfish, wahoo, and blackfin tuna IN .......
4 Bedrooms
- Sleeps 9
Vacation Rental in Big Pine Key
Pets Allowed 
SEA FOREVER! Gorgeous Ocean-Front Paradise!
Private Vacation Home in Big Pine Key
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 to you without any worries. This truly is paradise found!.......
5 Bedrooms
- Sleeps 12
Vacation Rental in Big Pine Key
Pets Allowed
Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
Private Vacation Home in Big Pine Key
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, bikes, SU paddleboards available. Beach/National Seashore park just minutes away. Charters nearby to Looe Key Marine Sanctuary reefs for snorkeling o.......
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
Private Vacation Home in Big Pine Key
Absolutely stunning, OCEANFRONT, dream home with panoramic views like none other. Truly one-of-a-kind property. Oceanfront POOL.
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 800 sqft of covered oceanfront decks/porches/balconies.
Our dream kitchen features an 8-seat, 9’ x 5’ quartz island with ocean views abounding. Our great.......
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations!
Private Vacation Home in Big Pine Key
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.
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 vesse.......
Discounted July- ocean-ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
Private Vacation Home in Big Pine Key
You have found it. So quiet. So peaceful. 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 unit with a full bath, kitchen, living room, and dining area downstairs. There is plenty of outdoor space on your private oceanfront beach .......
Gorgeous Beachfront Home with a pool. Water views from every direction.
Private Vacation Home in Big Pine Key
Step into your own island paradise! Welcome to this 5 bedroom 3 bath home. Featuring a large 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 kayaking to the other islands or snorkeling right off your beach or watch the Sea turtles come ashore. Close to everything and just far enough away! A must for nature lovers! 2 King beds, 2 .......
Dates available Oct, Nov, Dec 2023
Private Vacation Home in Big Pine Key
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 garage. 2 deep freezers and an extra fridge for bait available in the garage for your usage. An ice maker is inside the home. Wonderful chef’s kitchen........
Private water front property with ocean access
Private Vacation Home in Big Pine Key
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 beaches and Bahia Honda state park.
Also have over 30 ft of docking for your boat needs.
Great Location over all ! You will fall in love with ou.......
Upscale ocean front home & easy canal boat access to Gulf or Atlantic
Private Vacation Home in Big Pine Key
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 kitchen area opens up to three large sliding glass door windows giving an expansive view of the Bogie Chanel and No Name Key.
Within a 5 minute d.......
House 2 bedroom 2 bath Large enclosed porch overlooking canal with boat dock
Private Vacation Home in Big Pine Key
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........
2 Bedrooms
- Sleeps 6
Vacation Rental in Big Pine Key
Excellent boating location-65 ft frontage on deep canal
Private Vacation Home in Big Pine Key
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 tackle store is at the end of the street.
Outdoor amenities include a locked downstairs storage room, large bait freezer, fish cleaning table .......
BRILLIANT VIEWS OF OPEN WATERS- 75' DOCK - 250 ' TO OPEN CHANNEL BIG PINE KEY FL
Private Vacation Home in Big Pine Key
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 deck offers breath taking expansive views of the peaceful canal and beautiful Pine Channel. Relax at night with your favorite drink and marvel at the.......
Beautiful Family Big Pine Retreat! Short drive to Key West!
Bed & Breakfast in Big Pine Key
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 life consider booking our gorgeous Big Pine Retreat!.......
3 Bedrooms
- Sleeps 8
Vacation Rental in Big Pine Key
Big Pine Getaway - Pets + Boats Welcome
Private Vacation Home in Big Pine Key
Experience modern coastal luxury in this brand-new Big Pine Key home. Just minutes from Bahia Honda’s white-sand beaches and turquoise waters, this serene retreat features a sleek kitchen with stainless appliances, a cloud couch, smart TVs, and a stylish balcony. Unwind by the firepit under the covered terrace or stroll to the waterfront park. Pet friendly, pristine, and less than 30 minutes from vibrant Key West........
Florida Keys Water Front Vacation Home with Pool
Private Vacation Home in Big Pine Key
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 grill your fresh catch of the day! This house is a great place to host a group dinner or have a romantic evening.
The house is located 25 miles.......
3 Bedrooms
- Sleeps 6
Vacation Rental in Big Pine Key
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters
Private Vacation Home in Big Pine Key
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.
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 jus.......
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
Private Vacation Home in Big Pine Key
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.
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 yo.......
Escape the Ordinary and Experience Island Paradise
Private Vacation Home in Big Pine Key
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. Bicycles are provided for guest use to explore the neighborhood.
The home features an Open Concept living area, spacious King Suites, Walk-in Clo.......
Tropical Canal-front Cottage in the Lower Florida Keys
Private Vacation Home in Big Pine Key
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 Name Pub and Restaurant. Tie up a smaller boat or drop in your paddle boards and kayaks for a fun outing.
The villa features open concept living.......
2 Bedrooms
- Sleeps 8
Vacation Rental in Big Pine Key
Pets Allowed
Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home
Private Vacation Home in Big Pine Key
Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home. 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 King bed, queen bed, full bed. Bedrooms have soft bed linens, ceiling fans, and wall-mounted tv's. Relax in comfortable shade downstairs on a lounger, or the cozy sofa set, while you grill your catch.
Your p.......
3 Bedrooms
- Sleeps 6
Vacation Rental in Big Pine Key
Pets Allowed
Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly!
Private Vacation Home in Big Pine Key
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.
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 perfect.......
Find the Top Vacation Rentals in Big Pine Key, Florida Keys.
We have 2,3 or 4 Bedroom Homes with ocean view for the entire family. Book Direct Here!
Big Pine Key has beautiful scenery and offers lots of tranquility. There are plenty of outdoor activities that you can enjoy, such as fishing, walking and biking. It is located close to Key West and many people visit Big Pine Key for excellent snorkeling and diving.