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Vacation Rentals in Florida Keys

Find the perfect Cheap Vacation Rentals, Vacation Rental Deals and Luxury Villas in Florida, Colorado, California, Hawaii, South Carolina, Outerbanks and more! Get Last Minute Deals on Beach Houses, Ski cabins, Family Vacation Rentals and Pet Friendly Vacation Rentals now at How2Vacation.com!

Vacation Rentals in Florida Keys

Futura Yacht Club 101A

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 7 DAYS NEW LISTING – 3 bedroom/2 bath condo in highly desirable condo complex! Spend a week or…
  • from
  • $1025
    weekly

 

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

 

Cuban Paradise

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Cuban Paradise – Old Town Escape the stress and cares of your daily life Built in 1917 as a “club”…
  • from
  • $228
    nightly

 

Heather’s Villa

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • Heather’s Villa – Old Town Upon entering, the living room features a super comfy queen sleeper sofa if you choose…
  • from
  • $188
    nightly

 

Belle Fleur

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • Belle Fleur – Old Town Amenities: Parking: One off-street spot reserved, on-street parking also available. Sleeping Arrangements: Restrictions: Smoking only…
  • from
  • $5500
    monthly

 

La Bonne Vie

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • La Bonne Vie – Old Town Located only five blocks from infamous Duval St, this beautiful three story town home…
  • from
  • $5500
    monthly

 

Sunset Marina Paradise

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Sunset Marina Paradise – Stock Island is just that – a sunset paradise! Each night tells a different story. Located…
  • from
  • $4500
    monthly

 

Key West Conch

  • 3 Bedrooms, 1.5 Bathrooms, Sleeps 6
  • Key West Conch – Old Town This grandiose historic home was built in the 1890′s and has been host to…
  • from
  • $3500
    monthly

 

Artists Retreat

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Artists Retreat – Old Town This spacious and fully equipped unit is great for a vacationing family or small group…
  • from
  • $6500
    monthly

 

Casa Familia

  • 3 Bedrooms, 2 Bathrooms, Sleeps 4
  • Casa Familia – Old Town Enjoy this wonderful historic home with recent renovations, perfectly placed pool, separate master suite and…
  • from
  • $5000
    monthly

 

Casa Cayo Hueso

  • 3 Bedrooms, 2 Bathrooms, Sleeps 8
  • Casa Cayo Hueso – Old Town, which means “Key West House”, is a perfect example of shotgun architecture with a…
  • from
  • $3500
    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 122

  • 2 Bedrooms, 2.1 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 7 NIGHTS. Exceptional end unit townhouse with endless bay views from two balconies - one off the living…
  • 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

 

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

 

Casa Dulce

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Casa Dulce – Old Town This historic Conch House has been completely redesigned and custom crafted by 2 architects as…
  • from
  • $4000
    monthly

 

Maison du Soleil

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Maison du Soliel – Old Town means House of Sun. Recently renovated this contemporary condo with sixteen windows is not…
  • from
  • $3200
    monthly

 

Carey’s Cottage

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • Carey’s Cottage – Old Town Located right next door to the Five Brothers Grocery (the best con leche and Cuban…
  • from
  • $4000
    monthly

 

Tropical Retreat

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • Tropical Retreat – Old Town Enjoy this wonderful historic home with recent renovations, perfectly placed pool, separate Pool House and…
  • from
  • $5000
    monthly

 

Olé Olivia!

  • 4 Bedrooms, 3.5 Bathrooms, Sleeps 6
  • Olé Olivia! – Old Town You will be delighted with this wonderful home with recent renovations, perfectly placed pool, and…
  • from
  • $5500
    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
  • $950
    weekly

 

BEACON REEF 302

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 27 NIGHTS (ONE MONTH). Beautiful condo - new on the rental market. You'll be so glad the owners…
  • from
  • $3700
    monthly

 

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
  • $3500
    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
  • $2200
    monthly

 

Vista Linda-2 Master Suites -Private Pool, Spa, Dock, Sunsets in…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Vista Linda! Renovated 2011 to create two large beautiful suites with private baths, TVs and seating. One master bedroom has…
  • from
  • $1700
    weekly

 

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

 
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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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