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 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

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

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 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

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

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

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 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

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

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

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

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

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 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

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

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 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

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

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

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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