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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida Keys. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Big Pine Key house

Sandy Beach

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 ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

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Big Pine Key mobile home

Vacation Home

Beautiful Trailer in Big Pine Key

Trailer in beautiful Big Pine Key with great fishing, breezes, and relaxation. Brand new with 2 bedrooms, 1.5 bath, kitchen and huge living room. jbwihbiwnciuncubdweuyfbcwey8acweiucniunuiewncaiuodbcuhabhuewbcienwCIUABWDCUYHNAEWU9CNAEIOUWNIPWNCUHEWNC ....

2 Bedroom(s) 2 Bath(s) Mobile Home
Big Pine Key, FL

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Big Pine Key mobile home

Pelican Cove

Keys paradise hidden gem. Only 30 miles from Key West. Relax Relax Relax!

Located just 5 miles from Bahia Honda park rated top 5 beaches in the nation Located just 30 miles from famous Key West. Near Looe Key one of the worlds most beautiful snorling reefs. Enjoy the Key deer as they frequently come through this spacious s ....

3 Bedroom(s) 3 Bath(s) Mobile Home - Sleeps 6
Big Pine Key, FL

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Big Pine Key house

Vacation Home

Welcome to Casa Del Mar

Welcome to "Casa Del Mar" 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 al ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Big Pine Key, FL

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Big Pine Key house

TROPICAL VACATION HIDEAWAY

Tropical Vacation Hideaway - Viisit Paradise

This waterfront stilt home is on a boating canal just five minutes at idle speed from Boggie Chanel, with imediate access to the Atlantic or the Gulf of Mexico. The home is decorated to give you a resort feeling, with tropical and nautical style d ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL

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Big Pine Key house

Blue Heron Estate

Awesome Open Water View at Blue Heron Estate

Hurricane repairs are complete for the Blue Heron Estate. This is a 15 acre open water property with a 4 bedroom/4 bath house, a large pool and 70' of protected dockage. The grounds are a little rough but the views from the house of the open water an ....

4 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 10
Big Pine Key, FL

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Big Pine Key house

Keys Getaway

Beautiful Keys Getaway! Located on deep water canal for quick access to

This is a 2 bedroom, 2 bathroom concrete block house. It is located on a clean swimming canal right off Pine Channel. This Big Pine Key home has an open floor plan with updated kitchen, dinning room and living/TV room. The master bedroom has a Kin ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

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Big Pine Key house

Vacation Home

Perfect Keys Getaway

Beautifully furnished two bedroom two bath canal home located in Big Pine Key. Fully equipped kitchen with granite counters and stainless appliances, washer & dryer. Master bedroom with king bed, second bedroom has a queen size bed. Sofa in living ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

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Big Pine Key house

Big Pine Key Florida Keys Home

Florida Keys House, on canal, Key Deer, boating to Atlantic or Gulf

Very Comfortable, well furnished, 3 bedroom, 2 bath, stilt home. Large screened in porch facing east (cool in evening) overlooking canal and dock. Fully equipped kitchen with range, oven, microwave, dishwasher, pots pans, coffee makers, toasters. Was ....

4 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

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Big Pine Key house

Doctor's Hideaway

Another day in paradise! Modern Keys home, with access to Gulf and Atlantic

-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. No more then two and 15 lbs and less. There are feeding and water ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL

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Big Pine Key house

Buck's Beachhouse Bungalow

Great Family Retreat Property in Big Pine Key

Welcome to Buck's Beachhouse Bungalow . . . bring the whole family and enjoy the best of the Keys. A large gated, fenced property with lots of room for entertaining downstairs canal front.  Great boating out to pine channel which is some of the best ....

4 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL

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Big Pine Key house

Paradise at Key Deer Preserve

Big Pine Key, FL Waterfront 3 Bedroom 2 Bath Sleeps 8 people

Bring your Boat! This 3 bedroom 2 bath elevated home sits on Big Pine Key with the ocean in the front and a deep water canal equipped with Davits in back. This cozy home can sleep up to 8 people. Master Bedroom has a King Bed, First Bedroom has a ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL

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Big Pine Key house

Fisherman's Dream

Snow birds welcome! Great fishing

Luxurious home on deep canal with 100' of dock for your boats. A Fisherman's dream fish cleaning station. Close access to open water. Ocean view home in a quiet neighborhood. Close to marina and grocery shopping. Each bedroom has a private porch ....

4 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 12
Big Pine Key, FL

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Big Pine Key house

Casa El Sueño

Canal Front Home in Big Pine Key

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 clos ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL

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Big Pine Key house

Vacation Home

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 ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Big Pine Key, FL

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Big Pine Key house

Vacation Home

Canal Front Paradise!

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 o ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

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Big Pine Key house

Gulfside Getaway

Awesome boating from this 3/2 pool home on Big Pine Key

This well-maintained three-bedroom, two-bathroom tropical hideaway is just minutes from Pine Channel and some of the best boating in the Lower Keys! Located in the quiet neighborhood of Port Pine Heights on Big Pine Key, you can truly get away from i ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

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Big Pine Key house

New Listing! Waterfront Gem w/ Pool & Boat Basin

New Listing! Waterfront Paradise w/ Pool, Boat Basin & Panoramic Ocean Views

** This brand-new listing may not have an abundance of guest reviews yet, but you can be assured of an exceptional stay. Thoroughly vetted, this home is professionally managed by TurnKey Vacation Rentals, two-time winner of the Travel Weekly Magellan ....

4 Bedroom(s) 4 Bath(s) Vacation Rental
Big Pine Key, FL

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Big Pine Key house

Aqua Paradise Dream

Paradise in the Perfect Package

Beautifully decorated 3 bed/2 bath canal front home located in Big Pine Key. Master bedroom with queen bed and attached master bathroom. Newly renovated master bathroom has a walk in shower. Second guest bedroom has plush queen bed. Third guest bedro ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 10
Big Pine Key, FL

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Big Pine Key house

South Seas Retreat

Family Friendly Home Nestled In A Quiet Subdivision.

This is a Family Home located in the Port Pine Heights Area of Big Pine Key which sustained no damage due to Hurricane Irma. The home is on a Canal with concrete seawall and davits. Minutes to the Back Country and minutes to the Ocean for GREAT FIS ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

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Big Pine Key house

Vacation Home

Water Front Florida Keys Vacation Home

Quiet and comfy 3/2 water front home newly renovated. Enjoy all the wonderful amenities this home has to offer including fishing from your back yard or simply enjoying the view, ice maker for your freshly caught fish, BBQ grill, fish fryer, enjoy S'm ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

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