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Special Deals for Vacation Homes in the Florida Keys and Key West

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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

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

Vacation Home

Quaint Florida Keys home

We on Big Pine Key invite you to spend a little time with us and to experience the unique Florida Keys that is home to us. If total relaxation is your style then experience it keys style in the Lower Florida Keys. Walk through a nature trail with bir ....

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

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Big Pine Key cottage

Vacation Home

Beautiful Sunsets- Waterfront Paradise

BEAUTIFUL SUNSETS & QUICK BOAT ACCESS to Pine Channel. Experience Breathtaking Sunsets View and Escape to Your Own Private Corner of Paradise... This Island style waterfront cottage is lushly landscaped with unobstructed water views it offers wonde ....

2 Bedroom(s) 1 Bath(s) Cottage - 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

Florida Ocean Key

Florida Keys Pine Channel Water Front - Deep Canal

This concrete home is three doors down from the Pine Channel to the ocean. It’s located on one of the best deep water canal for great access to the Atlantic and/or back-country. This Lower Keys home has an open great room that includes the kitchen ....

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

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Big Pine Key mobile home

Vacation Home

Little Slice of Paradise

Newly remodeled 3 bedroom 2 bath in Big Pine Key. Perfect get away with everything you need for your home away from home. Spacious master bedroom with queen bed and private master bath. Second bedroom with queen bed and kids bunk bed room with twin ....

3 Bedroom(s) 2 Bath(s) Mobile Home - Sleeps 7
Big Pine Key, FL

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Big Pine Key recreational vehicle

Tropical Caribbean Wonderland

Tropical Caribbean Wonderland

Note: This is a new unit the other RV from the reviews was damaged by Irma and this is the NEW replacement unit it is AWESOME..!!! We are located in a beautiful RV wooded park, with endangered Key Deer everywhere you look. We have a nice Pool and cl ....

2 Bedroom(s) 1 Bath(s) Recreational Vehicle - Sleeps 4
Big Pine Key, FL

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Big Pine Key house

Captain D's Hideout

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. ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
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

Big Pine Oasis

Explore the Keys! Canal Front Property - Beautiful Sunsets

Conveniently located 10 miles from Bahia Honda State Park, 26 miles from Key West, 17 miles from Marathon, washer and dryer, dishwasher, microwave and oven/stove, direct tv, BBQ grill, outdoor shower, 2 car parking, in a quiet safe neighborhood. 52' ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
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

Casa Del Mar

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 , pool on deck. You can enjoy stunning oceanfront views from almost ever ....

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

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Big Pine Key house

BP Pool Getaway

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 ....

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

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Big Pine Key house

Big Pine Oasis

Explore the Keys! Canal Front Property - Beautiful Sunsets

Conveniently located 10 miles from Bahia Honda State Park, 26 miles from Key West, 17 miles from Marathon, washer and dryer, dishwasher, microwave and oven/stove, direct tv, BBQ grill, outdoor shower, 2 car parking, in a quiet safe neighborhood. 52' ....

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

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Big Pine Key house

Lobstertail Lair

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 shoppin ....

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

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Big Pine Key house

Time To Fish

Fisherman's Paradise in the Heart of Big Pine Key Deer Reserve

This waterfront vacation home is located in a quiet nature reserve, surrounded by several open undeveloped lots for extra privacy. 3 bedroom, 2 bath home with screen porch, and plenty of outdoor living area underneath. Master bedroom features king b ....

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

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Big Pine Key house

Starfish Retreat

Your Paradise Retreat in the Lower Florida Keys

Starfish Retreat is your slice of Paradise located on Big Pine Key, only a 25 minute drive from Key West. This two story home comfortably accommodates 6 guests . It has spacious bedrooms and bathrooms. The common area, which includes living room, din ....

3 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

DEER HAVEN

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 f ....

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

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Big Pine Key house

Key Deer Hideaway

Fantastic boating home perfect for your Florida Keys getaway!

Spacious 3 bedroom/2 bath home with 50 feet of dockage in the heart of the Key Deer Refuge on Big Pine Key. Energy efficient and quiet, with vaulted ceilings and brand new furnishings throughout. Large, fully equipped kitchen with granite countertops ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 7
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

Tarpon Bay

Tarpon Bay/Big Pine Key Tropical and Fishermans Paradise

Please note that we have a minimum 28 day rental period. - Excellent access to Gulf and Atlantic fishing and diving waters - 60' dock to accommodate boaters - Tropical setting with several species of palms - Large covered outdoor deck - King size b ....

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

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Big Pine Key house

Vacation Home

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - Boat lift , dock and fish cleaning station. -Excellent access to Atlantic and Gulf, minutes to the best lower keys fishing in coun ....

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

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Big Pine Key house

~CASA AZUL~

~CASA AZUL~ Brand new construction, deep water canal with pool!!!

OPEN WATER VIEWS FROM ALL ANGLES AND BALCONIES! Meticulously designed Keys home with exquisite furnishings throughout home, quartz counter tops and top of the line stainless steel appliances. This brand-new home has a lovely open & entertaining feel ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 13
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

Skelley House

Skelley - Quiet Cottage on corner canal

This 3 bedroom 2 bath home located on Big Pine Key is perfect for your Florida Keys Get-A-Way. Tropical canal front resort style home. Enjoy a beautiful open living room and kitchen, large lanai area with views of the canal and tropical landscape. ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 7
Big Pine Key, FL

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Big Pine Key house

Bogie Cottage

Fabulous boating access on Big Pine Key

Great spot for boaters! Newly remodeled and nicely appointed 2 bedroom/2 bath home on Big Pine Key. The master bedroom has a queen-sized bed, en-suite bath and walk-in closet. The second bedroom has two twin beds and ample storage. There's cable TV a ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
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

Big Pine Escape in Doctors Arm

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 ....

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

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Big Pine Key house

Reel Paradise

Reel Paradise - A Waterfront Boating Excape

Reel Paradise offer a large open format Keys retreat with vaulted ceilings, 3 bedrooms, 3 baths, dining room, large family room, sitting area, large screen plasma TV in the family room & private TV in each bedroom, 200 channel cable TV, DVD player, W ....

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

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