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Big Pine Key Vacation Rentals in the Florida Keys

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Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Big Pine Key, Florida.

We have partnered with a major provider for Vacation Rentals by Owner, directly through Florida Vacation Rental Homes. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida.


Vacation Rental - Big Pine Key Vacation House

Mickey and Lynn's House of Windows

Secluded two story above garage corner lot gives you a panoramic views of water and near by park. Key deer frequent the property on this lovely sanctuary. Over a hundred feet of dock space and cleaning table. Secluded but convenient, located close to variety of grocery stores, marinas and only 31 miles to Key West. Bedrooms: 3 Bathrooms: 3 Sleeps: 8 This house has in it a lovely that helps you forget .......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 8 House

Vacation Rental

Prime Time 2 - Big Pine Key Vacation House

Prime Time 2 - Charming Canal Front Duplex, Quick Trip to South Pine Channel And Atlantic or Gulf

Welcome to Prime Time 2! This charming waterfront duplex is located on Big Pine Key and offers quick open water access and a relaxing environment. Plenty of seawall for your boat and it's a short boat ride to world class fishing. Relax in the screened porch while reading a book or enjoying your favorite beverage! There's plenty to do in the Keys, you're only 40 minutes from Key West and 20 minutes from Marathon. If you need additional space, please check out our listing for Prime Time, as both sides of the duplex may be available to accommod.......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 6 House

Vacation Rental

Cedar Cottage - Big Pine Key Vacation House

2 bedroom accommodation in Big Pine Key

This newly remodeled 2 bed/2 bath home in Big Pine Key's Eden Pines neighborhood is the ideal place for your laidback Florida Keys vacation! Nestled in the quiet Key Deer Refuge on Big Pine Key, this home features a gorgeous, well-equipped kitchen with brand-new stainless appliances and tons of storage. Charming decor with warm wood floors. Brand-new bathrooms, including a huge shower in the master. Walk-around deck and large screened back porch, perfect for entertaining, with stairs down to the shady back yard and concrete dock. The master bed.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 4 House

Vacation Rental

Fishermen's Paradise - Big Pine Key Vacation House

Fishermen`s Paradise

Newly remodeled and with a brand-new dock, this spacious three-bedroom, four-bathroom home has a fantastic pool and amazing open-water views from every vantage point. Nestled in the backcountry on Big Pine, you'll enjoy the modern conveniences of this 2,000-square-foot elevated home while reveling in the natural areas surrounding it. The newly rebuilt 220-foot dock offers you some of the best boating access in the Lower Keys! The dock has a step-down on the end with a ladder for easier access. There's about 5 feet of draft. The updated kitche.......read more

4 Bedroom(s)
4 Bath(s) - Sleeps 8 House

Vacation Rental

Prime Time - Big Pine Key Vacation House

Prime Time - Tropically Themed Canal Front Duplex On Big Pine Key, Quick Access To Atlantic or Gulf

Welcome to Prime Time! This lovely canal front duplex is located on Big Pine Key and offers a fun, tropical vibe and open water access. Dock your boat along the sea wall and enjoy fantastic fishing only minutes away. Relax on the screened porch while enjoying your morning coffee or favorite cocktail as the boats go by! There's plenty to do in the Keys, you're only 40 minutes from Key West and 20 minutes from Marathon. If you need additional space, please check out our listing for Prime Time 2, as both sides of the duplex may be available to .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Tropical Beauty - Big Pine Key Vacation House

Special Tropical Beauty 3 BR Retreat -Pool-Dock-Tiki Hut

Saturday - Saturday Monthly Rental Open Lobster Dates July 1-31 or Aug 1-31 (No breaking months) This keys heated pool retreat is tucked away in a fantastic tropical paradise at Port Pine Heights, Big Pine Key. This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world . The gem like waters are the home of an almost endless variety of fish and marine life. In minutes you can explore the fantastic back country or Ocean by kayak or boat, or you can lay back and relax, away from it all and enjo.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 7 House

Vacation Rental

Captain D's Hideout - Big Pine Key Vacation House

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

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 sofas in the living room. New hi definition TV's, cable, Wi-Fi. Central air, wrap around deck. The canal leads out to Pine Chanel. Just a short scenic boat ride to the ocean or the Gulf. Lots of unin.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Vacation Rental - Big Pine Key Vacation Apartment

The Lookout on Big Pine Key

Message own for special rate on September or fall of 2020. Cute and cozy third floor one bedroom, one bathroom apartment with a kitchenette and living room. Great views of the sunset from the porch. View sunrise at the window by the breakfast table. The apartment has a private entrance and small porch. The Lookout is nicely decorated with exposed wood beam ceiling in the bedroom and wood flooring throughout. The property is located in the Key Deer nature preserve. We have a large wooded lot with a buttonwood hammock (pond covered with.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Apartment

Vacation Rental

Vacation Rental - Big Pine Key Vacation House

PARADISE IN YOUR HANDS

Beautiful clean and spacious home. Relax on your deck or take your boat out, canal goes out to the gulf or ocean to do some fishing or just water sports activities. Deer life all around. Mile marker 38 on Deer Key habitat and wildlife around. Great fishing, and enjoy all festivals with the locals. Great restaurants just a few minutes away. Key West is just a 35 min. drive, Bahia Honda 15 min. The best of paradise........read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Key Getaway ( BPK445 ) - Big Pine Key Vacation House

Keys Getaway

This spacious two-story Canal Front Home is located in Pine Channel Estate and offers fantastic boating access to some of the best fishing and diving/snorkeling spots in the Lower Keys. Tropical living at its best. The large screened porch is overlooking the canal. Master bedroom and loft sleeping area are on the second floor and have a queen bed each. The twin bedroom and queen bedroom are on the main floor. Lots of space to park your boat behind the home. Off-street car & trailer parking........read more

4 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Hidden Paradise - Big Pine Key Vacation House

3 bedroom accommodation in Big Pine Key

You'll relish your Florida Keys stay in this stilted canalfront home with ground-level guest suite, laundry and storage. There's a spacious, fully equipped kitchen with stainless steel appliances and an office setup for all your telecommuting needs. There are two queen bedrooms and two full bathrooms in the main floor, as well as a daybed with trundle and full bath with shower on the ground floor. Enjoy the outdoors on the screened porch or the spacious concrete dock. Fully fenced with 2 sets of entry gates, with parking in the carport or the o.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House

Vacation Rental

Big Pine Latitude Adjustment - Big Pine Key Vacation House

Big Pine Latitude Adjustment

Location location location! Room for the whole family in this gorgeous 5 bedroom 3 bath pool home on Big Pine Key. Home is basically all brand new, 100% remodeled floor to ceiling. Sleeps 10. Lounge out at the deep water pool which stays cool in the summer & heater is available for an additional charge in the winter. Over 200’ of concrete dockage space with quick access to Pine Channel with a 4’ draft – bring the big boat! Close to the Marina for fuel. Pack your bags, bring the boats & change your latitude! This is a 28-day minimum re.......read more

5 Bedroom(s)
3 Bath(s) - Sleeps 10 House

Vacation Rental

Manatee Watch - Big Pine Key Vacation House

4 bedroom accommodation in Big Pine Key

Brand new four-bedroom, three-bathroom boating home just four houses in from Pine Channel on the oceanside of Big Pine Key. There's a new concrete dock for your big boat and convenient steps into the water for swimming or paddle sports. There are 2 queen bedrooms and 2 full bathrooms on the main living floor and 2 huge queen bedrooms with a shared full bath on the top floor. There are two covered porches with peekaboo views of open water. Fully equipped kitchen with a breakfast bar that seats 3, plus a dining room table that seats six. Or enjoy.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 10 House

Vacation Rental

BP 3827 Dyer Rd - Big Pine Key Vacation House

SPECIAL TROPICAL POOL GETAWAY

This keys pool retreat is tucked away in a fantastic tropical paradise at Port Pine Heights, Big Pine Key. This lovely waterfront pool home has it all. This fantastic community is one of the most unique places in the world . This gated home sets on a huge property with plenty of room for your boats, trailers and cars. Neatly furnished you have the best of everything. You have a Flat screen TV , high speed internet , central air, huge private porch , outside gazebo. There is a neat living room group and a comfortable leather chair. The master .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 House

Vacation Rental

Casa Del Mar 305 5251254 - Big Pine Key Vacation House

Welcome to Casa Del Mar 305 5251254

Welcome to "Casa Del Mar" 305 5251254 a brand new mid-century modern home in Paradise! This home is a monthly vacation rental that must be rented for 28 days or greater. Quiet neighborhood , 3BR/2BA pool on deck. You can enjoy stunning oceanfront views from almost every room. For boaters ,fishermen and outdoors men feel free to use the 75 foot concrete boat dock with cleats, bumpers, fish cleaning table, bait freezer and tandem kayaks. There is a large island for entertaining and seating. The bedrooms are outfitted with, walk-in closets. For.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 12 House

Vacation Rental

Big Pine Key House - Big Pine Key Vacation House

Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!

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 or scuba diving. Local park nearby, as well as rest.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

BP Pool Getaway - Big Pine Key Vacation House

Tropical Waterfront Pool Getaway

This keys pool getaway is tucked away in a fantastic tropical paradise at Port Pine Heights, Big Pine Key. This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world. The gem like waters is the home of an almost endless variety of fish and marine life. In minutes you can explore the fantastic back country or Ocean by kayak or boat. Or you can lay back and relax, away from it all and enjoy a lovely tropical pool or drop a line off your private dock. It’s loaded with Mangrove Snapper. Neatly .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Bogie Cottage - Big Pine Key Vacation House

2 bedroom accommodation in Big Pine Key

Great spot for boaters! Newly remodeled and nicely appointed 2 bedroom/2 bath canalfront home on Big Pine Key. Everything you need for your time in paradise! There's a queen bed in the master and two twins with a king conversion kit in the 2nd bedroom. Good-sized closets. Flat screens in the living room and both bedrooms. The kitchen has everything you need for your stay. Gas grill and outside table downstairs. Concrete dock. Set on a canal right off Bogie Channel, the water access doesn't get any better than this. Heads up that the canal needs.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House

Vacation Rental

Prince's Keys Serenity - Big Pine Key Vacation House

Prince`s Keys Serenity

Beautifully remodeled, impeccably decorated and spacious ground-level home in the Tropical Bay neighborhood on the north side of Big Pine Key. Situated on a manicured triple lot at the end of a boating canal, it offers the perfect amount of social distance for your Florida Keys winter getaway.  This rental is only available November through April. Multi-month renter preferred. Discount offered for 6-month lease. The fully equipped, modern and roomy kitchen includes seating for two at the bar. The dining area has a table for six. Living room .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Natural Serenity - Big Pine Key Vacation House

2 bedroom accommodation in Big Pine Key

Enjoy uninterrupted natural vistas from this gorgeous home in one of the Lower Keys' best boating neighborhoods, Pine Channel Estates. This stilted canalfront home with ample concrete dockage on a clean, deep canal is just a few houses in from the channel and just 30 miles from Key West. There are no neighbors across the canal, just trees and key deer. This well-maintained and updated home features an open floor plan and a huge screened porch upstairs, with ample storage and and a fenced yard downstairs. The master bedroom features a large walk.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House

Vacation Rental

Sandy Beach - Big Pine Key Vacation House

Best Lower Keys Beachfront House and Dock on Florida Straits

Located directly on the Atlantic, this secluded home fronts one of the few natural sand beaches in the Florida Keys. The 165 foot long wooden dock has chickee for shade at the end. Sit and enjoy the sea breezes, watch the moon rise, or gaze out over the Florida Straits---you can almost see Cuba! Fish for the grand slam on the flats: tarpon/boneLsh/permit. Hunt for lobster and stone crabs, or spear snapper and grouper. Outside the reef, hook dolphin, sailfish, tuna, wahoo and more. Or fish the back country to the Gulf. Dive the patch reefs right.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Vacation Rental - Big Pine Key Vacation House

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House

Vacation Rental

Waterfront Home in The Keys! - Big Pine Key Vacation House

Waterfront Home in The Fabulous Florida Keys!

PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. We’d like to share our home with you. It’s a very spacious and clean 2 bedrooms, 2 bath home with an over sized master bdrm & bath. Cathedral ceiling in spacious living room that includes a queen size sleep sofa. Home is bright & airy. Wide, open covered deck with wrap around walkway. Home is on a 50ft wide canal and is just off of the Bogie Channel with easy access to the Gulf and Atlantic. Great fishing, lobstering, kayaking and diving. Concrete dock, fish cleaning s.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Big Pine Escape in Doctors Arm - Big Pine Key Vacation House

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

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 Loe 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 behind the house. This is a quiet residential area b.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Keys Living - Big Pine Key Vacation House

Nice 3 Bedroom / 2 Bath Canal Home in Big Pine Key

Florida "Keys Living", the way it should be!! Located in Doctor`s Arm, a very nice and quiet neighborhood. This 3 Bedroom / 2 Bathroom home that sleeps up to 8, is comfy, cozy and delightful. The fully-equipped kitchen is a pleasure to cook in for your family. A wrap-around upstairs deck and a screened-in porch just off the Dining Room, gives plenty of space for everyone. Outdoors at Keys Living is peaceful with swaying palm trees and wooden walkways leading to the canal front. Watch the fish swim by, observe the beautiful birds, or just sit .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Vacation Rental - Big Pine Key Vacation Recreational vehicle

Better than a tent

RV lot available with 27ft RV with full kitchen and bathroom, 1 bedroom with . queen bed and 2 bunks. at the other side. Full bathroom and kitchen and close to everything you need, like restaurants, stores, beach and watersports........read more

1 Bedroom(s)
2 Bath(s) - Sleeps 4 Recreational vehicle

Vacation Rental

DEER HAVEN - Big Pine Key Vacation House

SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT

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 aerial photos to see the space you will have during your stay. .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Vacation Rental - Big Pine Key Vacation House

Island Oasis

Welcome to Island living at its finest!! Not a detail has been spared in this home. Perfectly waterfront home located directly out to Bogie Channel for excellent deep sea fishing (Atlantic to your right and the gulf to your left). Walking distance to the famous No Name Pub, 25 minutes to Key West. Perfect home to relax with your family or jump on your boat right in your backyard and head out for some fishing. .......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 6 House

Vacation Rental

Changes in Latitude - Big Pine Key Vacation House

Tropical Getaway in the Florida Keys

Tropical getaway in Big Pine Key located on a canal that leads straight into Bogie Channel. Vaulted ceilings, open floor plan, master bedroom with walk in closet and private bathroom, 2nd bedroom has a double over double bunk bed plus a pull out trundle bed. Spacious hall bath, queen sofa bed in living room, and large screen porch make this a perfect spot for your next vacation. Rent a boat or kayak at the nearby Old Wooden bridge and keep on the canal to use on your vacation. Short walk to the No Name Pub for food and drinks. Two parks on .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 8 House

Vacation Rental

Reel NV - Big Pine Key Vacation House

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

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 Honda State Park, and a short boat ride to Looe Key, w.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Paradise Retreat ~ BPK - Big Pine Key Vacation House

Paradise Retreat ~ BPK

~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.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Lobstertail Lair - Big Pine Key Vacation House

Big Pine 2/2 ,Water Views and Sunsets Located Oceanside Now rentting 20 seas

Nice Quiet 2 bedroom 2 bath beach cottage located oceanside of US 1 on a swimming canal next to open water canal. Sunset and open water view. Boat slip to open water next door by same owner. New Kitchen and all furnishings 2010. Close to all shopping and activities On Big pine Key and a short drive to Key West without all the crowds. Beautiful sunsets from the outside patio overlooking the bay. In Immaculate condition and recently renovated. New in 2018 Bedrooms redone with new Lull memory foam beds , new windows and hardie Board siding for a.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House

Vacation Rental

5 O'Clock Somewhere - Big Pine Key Vacation House

***VERY NICE 3 BR / 2 BA CANAL HOME IN BIG PINE KEY!***

3 Bedroom/2 Bath Canal Home in Big Pine Key! Great boating location and easy access to open water. The home is very clean, well appointed and comfortable. Just bring yourself, your boat and some friends...you will be happy you picked 5 O'Clock Somewhere for your Florida Keys vacation home!.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House

Vacation Rental

Casa Del Mar 305 5251254 - Big Pine Key Vacation House

Welcome to Casa Del Mar 305 5251254

Welcome to "Casa Del Mar" (305) 5251254. a 3/2 brand new mid-century modern home in Paradise! This home is a monthly vacation rental that must be rented for 28 days or greater. Quiet neighborhood , pool on deck. You can enjoy stunning oceanfront views from almost every room. For boaters ,fishermen and outdoors men feel free to use the 75 foot concrete boat dock with cleats, bumpers, fish cleaning table, bait freezer and tandem kayaks. There is a large island for entertaining and seating. The bedrooms are outfitted with, walk-in closets. For y.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 12 House

Vacation Rental

Paradise at Big Pine - Big Pine Key Vacation House

New House Big Pine Key FL 60ft dock 1500ft to open waters of Pine Channel

Welcome to our new spacious 3 bedroom 2 full bath home on an 80 foot wide deep water canal with a 60 foot dock only 1500 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 canal enters Pine Channel south of the Overseas Highway Bridge ,so any guests with sailboats need not worry about clearance under the bridge to access the Atlantic Ocean. We have a 28 night minimum stay so that you have ample time to relax and truly have a memorable vacation . Our home .......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 8 House

Vacation Rental

Vacation Rental - Big Pine Key Vacation House

2/2 Canal Front Home with Great Boating Access! Located in Doctor’s Arm.

2 Bedroom 2 Bath Canal Front home on fenced lot with great boating access to back country or ocean side through Bogie Channel. Amenities include new A/C, upgraded master bath, & docking for your boat. Large screened in porch is perfect for sipping cocktails and watching the sunset. The house is located on Big Pine Key home to hundreds of friendly key deer which can be seen right in the front yard and throughout the neighborhood. We are a 5 minute walk from the famous No Name Pub and a 10 minute walk to No Name Bridge (beautiful early morning.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House

Vacation Rental

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