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

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

 

Our Island Thing - 4 Bedroom Family Vacation Home with…

  • 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
  • $5000
    monthly

 

Ocean Magic- 5 Bedroom Beachfront Vacation Home with Private Pool…

  • 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

 

2 Bedroom Vacation Home - Mango House in Florida Keys

  • 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- 3 Bedroom Pet Friendly Family Vacation Home in…

  • 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

 

3 Bedroom Vacation Home with Private Pool- Keys Escape in…

  • 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- Pet Friendly 2 Bedroom Vacation Rental in…

  • 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
  • $2300
    monthly

 

Ibis Landing- 3 Bedroom Vacation Home with Open Decks and…

  • 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 3 Bedroom Family Vacation Home Florida Keys

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of…
  • from
  • $2700
    monthly

 

Galleon Bay- 2 Bedroom Pet Friendly Vacation Home in 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 - 3 Bedroom Waterfront Vacation Home with 40…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Welcome to Egret's Landing! From the private balcony located off the master bedroom living area, to airy and vaulted ceilings,…
  • from
  • $2900
    monthly

 

Cudjoe Ocean Shores - 3 Bedroom Pet Friendly Island Vacation…

  • 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

 

2 Bedroom Waterfront Private Vacation Home- Cove Isle in 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- 3 Bedroom Vacation Home with Private Hot Tub…

  • 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- Luxury 3 Bedroom Family Vacation Home with Private…

  • 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 - 3 Bedroom Dockside Tropical Vacation Home in…

  • 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
  • Contact Owner

 

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 Del Sol- 3 Bedroom Waterfront Vacation Home with Private…

  • 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…
  • from
  • $5000
    monthly

 

Casa Caribe - 2 Bedroom Waterfront Vacation Home with Boat…

  • 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…
  • from
  • $2400
    monthly

 

Caribbean Dream- 4 Bedroom Waterfront Vacation Home - 3 Stories…

  • 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…
  • from
  • $5500
    monthly

 

Buttonwood - Pet Friendly 2 Bedroom Private Vacation Home with…

  • 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…
  • from
  • $1800
    monthly

 

Breeze Swept- 3 Bedroom Oceanfront Vacation Home with Private heated…

  • 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…
  • from
  • $5600
    monthly

 

Blue Marlin- 3 Bedroom Waterfront Vacation Home with Boat Dock!…

  • 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…
  • from
  • $3500
    monthly

 

Blue Heron - Romantic 2 Bedroom Canal Front Vacation Home-…

  • 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…
  • from
  • $2350
    monthly

 

Bay Pointe- Gated 3 Bedroom Family Vacation Home with Private…

  • 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…
  • from
  • $3800
    monthly

 

Barry Beach - 4 Bedroom Beachfront Family Vacation Home with…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • This Florida Style home was built in 1965 and wonderful surprises await you on the inside. The ground level house…
  • from
  • $2750
    weekly

 

Atlantis - 3 Bedroom Vacation Home! Florida Keys

  • 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…
  • from
  • $2800
    monthly

 

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…
  • from
  • $2200
    monthly

 

THE PALMS 506

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently…
  • from
  • $1800
    monthly

 

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…
  • from
  • $250
    nightly

 

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…
  • from
  • $4500
    monthly

 
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