Big Pine Key Vacation Rentals, Cottages & Private Rental Homes.

Big Pine Key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 8
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 4.9 Star Review

Beautiful, well maintained canal front home at the end of Big Pine Key. Surrounded by the Key Deer National Refuge. Wake up to Key Deer in your back yard. Only 30 miles from Key West and Duval Street. Concrete, step-down dock. Bring your boat. Great fishing and Diving. Bahia Honda Beach close by. Comfortably sleeps 6 plus two full sized sof.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

big pine key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 8
Vacation Rental Home in big pine key

Big Pine Key Vacation Rental

Luxury Airstream Travel Trailer fully equipped kitchen and bed linens. Book you stay and wake up to a water view every morning and sunsets by the canal every evening. Take advantage of the resorts large deck top pool, marina and boat docks. The general store is perfect for those last minute camping necessities........read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the exclusive Doctors Arm area of Big Pine Key, in the lower keys, just 25-miles from Key West. This water front property sits on a canal with easy access to the Gulf and Atlantic for some of the best fishing and lobster trapping in the world. The home is newly remodeled and high-te.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 12
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 4.7 Star Review

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 Bedrooms - Sleeps 8
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

~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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 9
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

Welcome to Heavenly Hideout!
YOUR FLORIDA KEYS CANAL FRONT HOME AWAITS...
NEW INGROUND POOL COMING BY DECEMBER 2023!!!
Vacation mode begins! Once you arrive at this lovely home, you'll be captured by the relaxing, fun outdoor space fully equipped with everything you'll want on vacation. Relax in one of the many seating areas downstairs or .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 4.9 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)

Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the exclusive Doctors Arm area of Big Pine Key, in the lower keys, just 25-miles from Key West. This water front property sits on a canal with easy access to the Gulf and Atlantic for some of the best fishing and lobs.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

- Pool and Tiki hut.
-2017 construction home on a 10,000 sf lot on a 40 foot wide canal.
-Please note that there is a 28 day minimum rental period for this property.
- Pet friendly for your fur babies. Size and number must be disclosed at booking. There are feeding and water bowls provided.
-Unsurpassed access to Gulf/back country an.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 2.5 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

-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 Bedrooms - Sleeps 8
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

Large outdoor kitchen , sitting area, corn hole activity area, swim spa , entertainment ( outdoor tv & outdoor speakers, Hammocks for relaxation. Keywest is 28 miles from Big Pine. The house in a quiet neighborhood and close to groceries stores and local restaurants &bars. Water access is 0.3 miles for all your boating activities. Master bedroom.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 4.6 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 4.9 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

Modern 3 bedroom 2 bath stilt home centrally located in Big Pine. Large heated swimming pool with tanning ledge. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store and Big Pine Park with tennis, basketball, skateboarding, racquetball, playground. Free public boat.......read more

4 Bedrooms - Sleeps 7
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. Its located in Tropical Estates, a quiet upper scale community with water access throughout. A perfect location if you are looking for a tranquil island setting but close to the fun as Key West is just 25 miles south. This home has 3 large bedrooms, 2 with 1 queen bed, .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

Welcome to Barnacle Bed and Breakfast, your seaside sanctuary where luxury, comfort, and adventure blend perfectly. This beachfront retreat offers plush rooms with ocean views, a private beach, and exquisite breakfasts. For those seeking adventure, complimentary kayaks and bicycles are at your disposal. Here, you'll wake up to the sound of waves, s.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

Enjoy unmatched privacy and serenity during your stay at this gorgeous canalfront 3 bedroom/3 bathroom pool home with brand new dock nestled near the end of Doctors Arm on Big Pine Key. Large custom concrete pool with heater for those cooler fall and winter nights. There are clear 40-foot-wide flow-through canals on two sides of this lushly landsca.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

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 Bedrooms - Sleeps 9
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

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 Bedrooms - Sleeps 12
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

Newly renovated, tranquil half-duplex nestled among the natural beauty of Big Pine Key! Enjoy an immaculately clean space that features all the comforts of home. Central air and ceiling fans in every room keep it super comfortable. The brand new kitchen is perfect for a lazy breakfast or dinner in.

The home features 2 bedrooms with 2 queen b.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 4.9 Star Review

This two bedroom two bath home open floor concept is very comfortable. Master bedroom has sliding doors to screened in balcony that faces canal. Has a private bath and large closet. Additional room has two twin beds with very spacious walk in closet. Living room,dinning room and kitchen are open floor plan which makes it very comfortable for fa.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 5.0 Star Review

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 Bedrooms - Sleeps 10
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

Discover The Lost Lobster: A Captivating 3-Bedroom/2-Bathroom Family Home on Big Pine Key!

The heart of this home embraces an open-concept design, where the living room, dining area, and kitchen seamlessly meld together. The kitchen boasts modern stainless steel appliances, an inviting island, and a dining table that comfortably seats four (.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

Here is a unique and tranquil getaway that is the best of all worlds. Enjoy setting in the soft tropical breezes that overlooks the Key Deer Refuge providing privacy. The home is a boaters delight with a 40ft seawall. This quiet location offers quick access to the Atlantic or back country water, close to world class fishing, beautiful sand bars and.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

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 Bedrooms - Sleeps 8
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental

Do everything or nothing at this Florida Keys 2br/2ba! Relax on the screened porch, kayak in the canals or take a boat ride from your dock. Open water access for fishing & watersports is just 12 minutes away. Famed Key Deer are abundant in the neighborhood during walks & bike rides, be at Bahia Honda State Park beaches in 15 minutes or be in Key We.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key

Big Pine Key Vacation Rental 4.8 Star Review

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 Bedrooms - Sleeps 6
Vacation Rental Home in Big Pine Key