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

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 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 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

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

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

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

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

~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

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

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 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

Eagles Nest

Eagles Nest- Corner canal front home with screened in balcony

The corner canal front home is located on Big Pine Key in the Fabulous Florida Keys. 3 bedroom 3 bath home with seawall and screened in porch. 3 bedroom/2 bath Canal Front Home on Big Pine Key with large sea wall and screened in porch. Boats are li ....

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

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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

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

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

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

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 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 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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