Vacation Rentals in Florida Keys

Ocean Breeze

• 3 Bedrooms, 2 Bathrooms, Sleeps 6
• LAST-MINUTE SPECIAL! 20% OFF ANY MONTH JANUARY 2013-APRIL 2013 IF BOOKED BY 12/31/12 MINIMUM STAY: 29 DAYS BEAUTIFUL CANAL FRONT…

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• $3500
  monthly
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Sunset Hammock 7B

• 2 Bedrooms, 2.5 Bathrooms, Sleeps 6
• MINIMUM STAY: 60 DAYS Relax and escape the hustle and bustle of city life or cold northern winters in the…

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• $2900
  monthly
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Casa Monte in Summerland Key Florida

• 4 Bedrooms, 3 Bathrooms, Sleeps 8
• This ocean front masterpiece was created for those who only want the very best. This multimillion dollar home boasts 4…

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• $6900
  monthly
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Casa Grande in Summerland Key Florida

• 3 Bedrooms, 3 Bathrooms, Sleeps 6
• A vacation of a lifetime awaits you and your guests at Casa Grande. Just imagine lounging poolside on the crisp…

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• $6500
  monthly
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Casa Del Sol in Ramrod Key Florida

• 3 Bedrooms, 2 Bathrooms, Sleeps 6
• Sit back and relax in this delightful home, situated on the open water. The entire rear wall of this home…

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• $5000
  monthly
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Casa Caribe in Summerland Key Florida

• 2 Bedrooms, 2 Bathrooms, Sleeps 7
• This lovely 2 bedroom, 2 bath residence is located on Summerland Key at mile marker 24 just north of Key…

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• $2400
  monthly
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Caribbean Dream in Summerland Key Florida

• 4 Bedrooms, 3 Bathrooms, Sleeps 8
• This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. This beautiful home…

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• $5500
  monthly
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Buttonwood in Big Pine Key Florida

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• Just the right size at just the right price! Very comfortable and cute 2 bedroom, 2 bath home on Big…

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• $1800
  monthly
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Breeze Swept in Big Pine Key Florida

• 3 Bedrooms, 2 Bathrooms, Sleeps 6
• Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts décor…

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• $5600
  monthly
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Blue Marlin in Summerland Key Florida

• 3 Bedrooms, 2 Bathrooms, Sleeps 6
• Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 people in this…

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• $3500
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Blue Heron on Big Pine Key, Florida Keys Florida

• 2 Bedrooms, 2 Bathrooms, Sleeps 4
• Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation…

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• $2350
  monthly
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Bay Pointe in Key West Florida

• 3 Bedrooms, 3 Bathrooms, Sleeps 8
• Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of…

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• $3800
  monthly
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Barry Beach in Summerland Key Florida

• 4 Bedrooms, 3 Bathrooms, Sleeps 8
• Enjoy the ultimate in relaxation with this open-water home on Little Torch Key (gulf side) mile marker 29. This very…

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• $7200
  monthly
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Atlantis in Big Pine Key, Florida Keys Florida

• 3 Bedrooms, 3 Bathrooms, Sleeps 6
• Everyday is a great day at Atlantis. Beautiful Big Pine home located just minutes to Bogie Channel. This channel affords…

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• $2800
  monthly
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Maison du Calais

• 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
• Maison du Calais – Old Town Amenities: Heated Pool, Deck, Jacuzzi, Washer/Dryer, Dishwasher, DVD Player, High Speed Internet, Separate cottage…

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• $5000
  monthly
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Lost Weekend

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• Lost Weekend – Old Town is perfectly situated for the discriminating guest who wants to enjoy Key West at its…

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• $4500
  monthly
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Elgin Hideaway

• 2 Bedrooms, 2 Bathrooms, Sleeps 4
• Elgin Hideaway – Old Town Enjoy this beautiful 2 story historic home, sunny pool, large open floor plan for entertaining…

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• $4000
  monthly
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Casita Mango

• 1 Bedroom, 1 Bathroom, Sleeps 2
• Casita Mango – Old Town Casita Mango is a lovely retreat for your Key West stay, whether for one or…

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• $2750
  monthly
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Yellow on White

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Yellow on White – Old Town Yellow on White is conveniently located next to a full spa to relax your…

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• 0 Bedroom, 0 Bathroom, Sleeps 0

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Windsor Townhome #1

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Windsor Townhomes – Old Town Elegance and modern sophistication are apparent as you enter any one of these six newly…

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• $458
  nightly
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Secret Courtyard Cottage

• 2 Bedrooms, 1 Bathroom, Sleeps 5
• Secret Courtyard Cottage -Old Town Welcome to a little piece of hidden paradise you never knew existed. Once you’re nestled…

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• $275
  nightly
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Bella Vita

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Bella Vita – Old Town Located half a block from infamous Duval St, this beautiful 1 bedroom, one bathroom property…

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• $188
  nightly
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Paradise Harbor Retreat

• 3 Bedrooms, 3 Bathrooms, Sleeps 6
• Paradise Harbor Retreat – Old Town This gorgeous four level home is a luxurious waterfront property. It is a spacious…

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• $550
  nightly
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The Palms 402

• 2 Bedrooms, 2 Bathrooms, Sleeps 5
• MINIMUM STAY: One Month. Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You’ll love the uncluttered…

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• $2200
  monthly
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THE PALMS 506

• 2 Bedrooms, 2 Bathrooms, Sleeps 4
• MINIMUM RENTAL: 28 DAYS. Wonderfully inviting condo at one of Islamorada's favorite condo complexes. This unit is tastefully decorated with…

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• $1800
  monthly
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VILLA BELLA 13

• 3 Bedrooms, 3 Bathrooms, Sleeps 8
• MINIMUM RENTAL: 3 NIGHTS. Villa Bella is a fabulous 3 BR/3 BA two-story townhouse. This end unit townhome “lives” on…

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• $250
  nightly
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VALENCIA GETAWAY

• 3 Bedrooms, 2 Bathrooms, Sleeps 8
• MINIMUM RENTAL: 29 DAYS. Bring your boat your dog and the kids! Relax on the patio or swim in the…

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• $3400
  monthly
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Angelfish Cove in Big Pine Key Florida

• 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
• Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of…

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• $3600
  monthly
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Red on White

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Red on White – Old Town Located in the heart of the White Street art district, just six blocks from…

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• $128
  nightly
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Purple on White

• 1 Bedroom, 1 Bathroom, Sleeps 2
• Purple on White – Old Town Located on White street just six blocks from both Duval Street and the Historic…

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• $128
  nightly
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Green on White

• 1 Bedroom, 1 Bathroom, Sleeps 3
• Green on White– Old Town Green on White is located just six short blocks from both Duval street and the…

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• $128
  nightly
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Blue on White

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Blue on White– Old Town Blue on White is located in the heart of the White Street art district, just…

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• $128
  nightly
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Windsor Townhome #5

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…

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• $458
  nightly
• 
  Compare

Buena Vista

• 1 Bedroom, 1 Bathroom, Sleeps 2
• Buena Vista – Old Town This wonderfully indulgent one bedroom cottage is on Center Street, just one-half block from Duval…

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• $178
  nightly
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Windsor Townhome #3

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…

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• $458
  nightly
• 
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La Casa De Luces

• 1 Bedroom, 1 Bathroom, Sleeps 4
• La Casa De Luces – Old Town Come to relax or to play while enjoying the spectacular sunsets and the…

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• $168
  nightly
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Heron Suite

• 1 Bedroom, 1 Bathroom, Sleeps 2
• Heron Suite– Old Town Tucked among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Heron Suite.…

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• $188
  nightly
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Royal Escape

• 3 Bedrooms, 3 Bathrooms, Sleeps 10
• Royal Escape – Old Town If Cleopatra and Anthony had dreamed of a Key West hideaway this spacious three bedroom,…

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• $458
  nightly
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Cuban Club Suite

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• Cuban Club Suite – Old Town Built in 1917 as a “club” for Cuban cigar makers and their families as…

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• $228
  nightly
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SEA GULLS 506

• 2 Bedrooms, 2 Bathrooms, Sleeps 4
• MINIMUM STAY: 7 DAYS. Charming 5th floor condo with panoramic views of the Atlantic Ocean from the balcony. New owner…

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• $850
  weekly
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SUMMER SEA 305

• 1 Bedroom, 1 Bathroom, Sleeps 4
• MINIMUM RENTAL: 30 DAYS. An "efficient" little condo unit in one of the nicest condos in the area. This bayfront…

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• $1400
  monthly
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PLANTATION BY THE SEA 121

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• MINIMUM RENTAL: 28 DAYS. Enjoy this beautifully remodeled two bedroom condo at Plantation by the Sea. Brand new kitchen (12/2010)…

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• $1900
  monthly
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Palm Harbor

• 4 Bedrooms, 3 Bathrooms, Sleeps 8
• MINIMUM RENTAL: 30 DAYS. Spacious elegant home with pool and dock. Gently swaying palm trees greet you at the gated…

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• $9975
  monthly
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The Palms 301

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• MINIMUM RENTAL: 28 DAYS. This exceptional condo has been impeccably maintained and is located in one of the finest condo…

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• $2000
  monthly
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LITTLE BAY COTTAGE

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• MINIMUM RENTAL: 3 NIGHTS. This is one of three rental units on this property. The cottage is a ground level…

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• $350
  nightly
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Casa Lorelane

• 7 Bedrooms, 5 Bathrooms, Sleeps 24
• This home is for the guests who expect extraordinary accommodations. Plan your dream vacation now to The Florida Keys and…

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Island Time 2 in Big Pine Key, Florida Keys Florida

• 3 Bedrooms, 1 Bathroom, Sleeps 6
• Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge…

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• $2200
  monthly
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Windsor Townhome #2

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…

• from
• $458
  nightly
• 
  Compare

Tortuga Hammock

• 2 Bedrooms, 3 Bathrooms, Sleeps 4
• Tortuga Hammock – Stock Island Not even 1 mile from Key West proper, this gem is hidden right off of…

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• $258
  nightly
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