Vacation Rentals in Florida Keys

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Vacation Rentals in Florida Keys

Turtle Time

  • 3 Bedrooms, 2 Bathrooms, Sleeps 7
  • MINIMUM STAY: One Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home!…
  • from
  • $3800
    monthly

 

Summer Isle in Summerland Key, Florida Keys Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Surrounded by lush, tropical landscaping, this gated open-water vacation home comes equipped will all the thoughtful touches of home and…
  • from
  • $6900
    monthly

 

Sea Breeze in Summerkey, Florida Keys Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Clean, sharp lines outline this welcoming vacation home located on a clean, clear deepwater canal. Easy access to some of…
  • from
  • $2700
    monthly

 

Quiet Waters in Cudjoe Key, Florida Keys Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This Cudjoe Key home is neat as a pin. Brand new in 2007 with all the comforts of home. Bright…
  • from
  • $2400
    monthly

 

Pirate's Cove in Cudjoe Key, Florida Keys Florida

  • 2 Bedrooms, 1 Bathroom, Sleeps 4
  • Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and…
  • from
  • $2000
    monthly

 

Palm Villa in Little Torch Key, Florida Keys Florida

  • 2 Bedrooms, 2.5 Bathrooms, Sleeps 6
  • This beautiful custom home located in Jolly Rodger subdivision on Little Torch Key has the best of everything. Just furnished…
  • from
  • $5200
    monthly

 

Key Largo Townhome

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 30 DAYS Exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring…
  • from
  • $3200
    monthly

 

LITTLE BAY - Lower Duplex

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 3 NIGHTS. This is one of three rental units on this fabulous property. The Little Bay property is…
  • from
  • $350
    nightly

 

LITTLE BAY - Upper Duplex

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 3 NIGHTS. This is one of three rental units on this fabulous property. The Little Bay property is…
  • from
  • $350
    nightly

 

FUTURA YACHT CLUB 722

  • 2 Bedrooms, 2.1 Bathrooms, Sleeps 4
  • Minimum Rental: 7 Nights Beautiful end unit townhouse with marina and bay views from two balconies - one off the…
  • from
  • $950
    weekly

 

MOON BAY B404

  • 2 Bedrooms, 1.5 Bathrooms, Sleeps 5
  • MINIMUM RENTAL: 7 NIGHTS. Unwind and enjoy the Sunsets on the Florida Bay! Full wall of glass overlooking the pool…
  • from
  • Contact Owner

 

BEACON REEF 501

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from…
  • from
  • $3200
    monthly

 

Paradise Bay in Cudjoe Key, Florida Keys Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This great vacation home is conveniently located on Cudjoe Key. The all tile kitchen is fully equipped and living &…
  • from
  • $2750
    monthly

 

Our Island Thing in Big Pine Key, Florida Keys Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This tropical paradise is just waiting for you and your guests. Located near the end of a quiet lane this…
  • from
  • $3200
    monthly

 

Ocean Magic in Summerland Key, Florida Keys Florida

  • 5 Bedrooms, 5 Bathrooms, Sleeps 10
  • A tranquil oasis is your destination at Ocean Magic, with tropical Caribbean waters right out your door. This estate quality…
  • from
  • $13500
    monthly

 

Mango House in Big Pine Key, Florida Keys Florida

  • 2 Bedrooms, 1.5 Bathrooms, Sleeps 4
  • Simple and sweet with no muss, no fuss. It's all right here - Gulf Side! This quaint two bedroom vacation…
  • from
  • $1800
    monthly

 

Manatee Bay in Big Pine Key, Florida Keys Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends…
  • from
  • $2500
    monthly

 

Keys Escape in Cudjoe Key, Florida Keys Florida

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • Escape from all your cares at this wonderful vacation rental on Cudjoe key. Just the spot to unwind and let…
  • from
  • $4500
    monthly

 

Island Time 1 in Big Pine Key, Florida Keys Florida

  • 2 Bedrooms, 1 Bathroom, Sleeps 4
  • Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge…
  • from
  • $2200
    monthly

 

Ibis Landing in Sugarloaf Key, Florida Keys Florida

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Ibis Landing is truly a remarkable property nestled by the Great White Heron Wildlife Refuge. Acres of nature's wonders can…
  • from
  • $3900
    monthly

 

Gulf Shores in Summerland Key, Florida Keys Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Sit back and relax in this clean, airy, and spacious vacation home. Located on a canal and equipped with all…
  • from
  • $2700
    monthly

 

Galleon Bay in Cudjoe Key, Florida Keys Florida

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Galleon Bay on Cudjoe Key is the perfect spot to enjoy your Florida Keys vacation. This home is centrally located…
  • from
  • $2500
    monthly

 

Egret's Landing in Cudjoe Key, Florida Keys Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • From the private balcony located off the master bedroom living area, to airy and vaulted ceilings, this Cape Cod style…
  • from
  • $2900
    monthly

 

Driftwood Manor in Sugarloaf Key, Florida Keys Florida

  • 5 Bedrooms, 5 Bathrooms, Sleeps 10
  • Step back in time to the days when style and craftsmanship were the order of the day. The simple elegance…
  • from
  • $7000
    monthly

 

Cudjoe Ocean Shores in Cudjoe Key, Florida Keys, Florida

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Enjoy the rustle of swaying palms and the balmy tropical breezes from the screened and tiled balcony of this immaculate…
  • from
  • $2700
    monthly

 

Cove Isle in Summerland Key, Florida Keys Florida

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great…
  • from
  • $2800
    monthly

 

Coral House in Ramrod Key, Florida Keys Florida

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile…
  • from
  • $3000
    monthly

 

Cayo Villa in Summerland Key, Florida Keys Florida

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home…
  • from
  • $7500
    monthly

 

Casa Rosado in Kudjoe Key Florida

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This beautiful, vacation home is tropical, bright and confortable. You'll wish it was your own! Kitchen is fully equipped with…
  • from
  • $4800
    monthly

 

Sunshine Place

  • 1 Bedroom, 1.5 Bathrooms, Sleeps 2
  • MINIMUM STAY: 7 Days. You can have it all – privacy and convenience. The owners of this wonderful property called…
  • from
  • Contact Owner

 

BEACON REEF 314

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 28 DAYS. Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in…
  • from
  • $3300
    monthly

 

BEACON REEF 222

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: 30 DAYS. Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your private balcony…
  • from
  • $4000
    monthly

 

BEACON REEF 211

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 28 DAYS. This is a very special unit in a premier condominium complex located directly on the Atlantic…
  • from
  • $4000
    monthly

 

Sunset Hammock 4B

  • 2 Bedrooms, 2.5 Bathrooms, Sleeps 4
  • MINIMUM STAY: 60 DAYS. Immaculate townhouse in prestigious Sunset Hammock in Tavernier. You’ll enjoy your time in the Keys in…
  • from
  • $2300
    monthly

 

The Palms 214

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 28 DAYS. Gorgeous 2 bedroom, 2 bath condo. The Palms of Islamorada is gated for privacy and located…
  • from
  • $2000
    monthly

 

Matecumbe Jewel

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Minimum stay 29 Days. You will love this home! This is a jewel of a home. Located in Lower Matecumbe…
  • from
  • $4000
    monthly

 

The Palms 201

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Minimum Rental: 28 days. Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations.…
  • from
  • $2000
    monthly

 

THE PALMS 314

  • 2 Bedrooms, 2 Bathrooms, Sleeps 5
  • Minimum Rental: 28 days. Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully…
  • from
  • $2200
    monthly

 

Brock Haus on the Gulf

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge…
  • from
  • $1200
    weekly

 

Emerald Cove

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • MINIMUM STAY: 29 DAYS. You‘ll love watching the fabulous sunsets over the tranquil waters in this semi-private lagoon setting. This…
  • from
  • $5500
    monthly

 

Moon Bay Condo A206

  • 2 Bedrooms, 1.5 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 7 NIGHTS. Whether you plan to fish or dive on your next visit to the Keys, you will…
  • from
  • Contact Owner

 

Blue Water Retreat

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Minimum Rental 29 Days. Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled…
  • from
  • $5000
    monthly

 

My Paradise

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Minimum Rental 29 Days. Direct oceanfront home with large sandy beach, protected dockage , handicap accessible and located in the…
  • from
  • $6500
    monthly

 

Twice the Charm

  • 4 Bedrooms, 3 Bathrooms, Sleeps 12
  • Minimum rental: 28 nights. Enjoy your stay in this gorgeous single family home. You'll love the convenient location in the…
  • from
  • $3500
    monthly

 

The Palms #403

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: One Month This exceptional 2 bedroom and 2 bath condo is located in one of the most popular…
  • from
  • $2400
    monthly

 

Villa Riolo

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in…
  • from
  • $3000
    monthly

 

Bayside Breeze

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 30 DAYS NEW HOME (2013) The simple and uncomplicated design of this home with 3 ample sized bedrooms…
  • from
  • $4200
    monthly

 

Ocean Breeze

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 29 DAYS BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this…
  • from
  • $4000
    monthly

 

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…
  • from
  • $2900
    monthly

 

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…
  • from
  • $6900
    monthly

 
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SeaBird Key

Escape to Seabird Key and immerse yourself in the dream. Your own private island getaway...a place abundant with beauty, privacy and ultimate tranquility, located in the heart of the Florida Keys.



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