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

Waterfront Paradise

Waterfront Big Pine Key Paradise

House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6) Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the exclusive Doctors Arm area of Big Pine Key, in the lower keys, just 25-miles from Key West. This water front property s ....

3 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

Pine Channel Getaway

BIg Pine Key New House 75 ft dock 250 feet from open waters of Pine Channel

Welcome to our new spacious 3 bedroom 2 full bath home on a wide deep water canal with a 75 foot dock only 250 feet from the peaceful open waters of Pine Channel. Our comfortable 10 ft by 20 ft rear deck offers breath taking expansive views of the pe ....

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

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

~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

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

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

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 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

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

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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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 mobile home

Pelican Cove

Keys paradise hidden gem. Only 30 miles from Key West. Relax Relax Relax!

Located just 5 miles from Bahia Honda park rated top 5 beaches in the nation Located just 30 miles from famous Key West. Near Looe Key one of the worlds most beautiful snorling reefs. Enjoy the Key deer as they frequently come through this spacious s ....

3 Bedroom(s) 3 Bath(s) Mobile Home - 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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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

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

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

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

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

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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