Short Term Vacation Rental Homes in the Florida Keys & 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

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

Tropical Beauty

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

Saturday - Saturday Rental 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 wor ....

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

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

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

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

Big Pine Key House

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

Beautiful, new 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 ....

4 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

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

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

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

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

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 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

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

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

Vacation Home

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

Sunrise on Tropical Bay

Recently remodeled 4 bedroom

Remodeled Ocean front with Boating and a POOL . This 4 bedroom, 3 1/2 bath, fully-furnished home is right on Bogie Channel on Big Pine Key. It has full ocean access and the time you spend exploring the Lower Key’s back country will be time you will ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
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

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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