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 - 3 Bedroom Oceanfront Vacation Home with Private…

  • 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 - 3 Bedroom Vacation Home on the Canal…

  • 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
  • $3100
    monthly

 

Quiet Waters - 3 Bedroom Family Vacation Home with Screened…

  • 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

 

Romantic 2 Bedroom Pet Friendly Vacation Home with Boast Dock!…

  • 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

 

3 Bedroom Vacation Home on the Canal- Palm Villa in…

  • 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

 

LITTLE BAY - Lower Duplex

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 7 NIGHTS. This is one of three rental units on this fabulous property. The Little Bay property is…
  • from
  • $2400
    weekly

 

LITTLE BAY - Upper Duplex

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 7 NIGHTS. This is one of three rental units on this fabulous property. The Little Bay property is…
  • from
  • $2400
    weekly

 

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
  • $5250
    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

 

PLANTATION ADVENTURE

  • 4 Bedrooms, 3 Bathrooms, Sleeps 10
  • MINIMUM STAY: 29 DAYS Sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB,…
  • from
  • $6750
    monthly

 

Largo Kai Ground Level

  • 1 Bedroom, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: 1 MONTH Only 1 - 4 people? Want something spacious but don't need a mansion? This is it!!…
  • from
  • $4950
    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) Spend the fall or winter in the Florida Keys! You will love this…
  • 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

 
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