Big Pine & Lower Florida Keys Vacation Rentals, Hotels & Resorts

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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 Lower 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

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

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 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

Catlin By The Sea

Catlin By The Sea Excellent Boating Location for Ocean and Back County Access

This canal front comfortable home is nestled in the North East Corner of Big Pine Key. Endangered Key Deer, found only in the keys, roam about the neighborhood as well as many other wildlife species. This property offers excellent boating with dire ....

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

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Big Pine Key house

Vacation Home

Open Water and Sunset Views Pool House in the Florida Keys

Newly renovated 4 bedroom 2 bath house on Big Pine Key. Property includes 35' dock, double lot, heated swimming pool, fire pit, BBQ, ice machine, downstairs storage, kayaks, paddleboards, cornhole boards and more! Master Bedroom upstairs with King ....

4 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
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

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

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

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

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

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

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 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 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 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

Nichols Key

Gorgeous 2 bedroom 2 bath canal front pool home

Gorgeous canal front 2 bedroom 2 bath pool home located on Big Pine Key. Excellent boating to the Gulf or the Atlantic with over 70' of concrete seawall. Mature landscaping surrounds the pool and tiki hut making it a tropical paradise The home featur ....

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

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Big Pine Key house

Vacation Home

Gulf and Atlantic access fishing and diving paradiss

Large and comfortable home located on canal with direct Bluewater access 10 min to Atlatic. 3 spacious bedrooms, great sleeping setup for kids. 3 minutes to grocery and shopping in big pine including dive store and tackle shops. 25 minute drive to Ke ....

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

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Big Pine Key house

The Blue Lagoon

The Blue Lagoon - A real cream puff!

Adorable vacation home in Port Pine Heights! Welcome to the Blue Lagoon . . . a beautiful, warm and inviting two bedroom, 2 bath coastal chic home in the ever popular Port Pine Heights. A quiet, serene setting with gorgeous sunset views from a full ....

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

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Big Pine Key house

Palm Ave 3/3

Experience the Keys like a Local at this Spacious Canal Front Home with Dock!

This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 40 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to enjoy the party atmosphere of Key West! Dock your boat o ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
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

Reel NV

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 ....

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

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Big Pine Key house

Vacation Home

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5 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 11
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

~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

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

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

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

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

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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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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Find Affordable Big Pine or Lower Florida Keys Oceanfront Hotels & Vacation Rentals

Plan your Big Pine and Lower Keys Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Big Pine and Lower Keys, Florida Keys.

Spend quality time with your family and friends at cheap low rates you can afford, all while near the beach, nightlife, entertainment and a wide variety of beach activities. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.

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