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

TROPICAL OASIS

  • 4 Bedrooms, 4 Bathrooms, Sleeps 10
  • MINIMUM STAY: 28 DAYS Exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas.…
  • from
  • $8500
    monthly

 

Fabulous 3 Bedroom Vacation Beach House - SEA GRAPE

  • 3 Bedrooms, 2 Bathrooms, Sleeps 7
  • MINIMUM STAY: 28 DAYS FABULOUS BEACH HOUSE with sea grape trees on three sides and the ocean on the other!…
  • from
  • $5500
    monthly

 

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…
  • from
  • $2500
    monthly

 

Comfortable 2 Bedroom Vacation Condo - Steps to Marina -…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM RENTAL: 27 NIGHTS (ONE MONTH). Comfortably furnished and ready for you. Conveniently located just steps from a full service…
  • from
  • $2000
    monthly

 

Charming 2 bedroom, 2 bath home with an open living…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Minimum Stay 1 Month. "Beba's Reef House" will capture your imagination the moment you enter the home and rise to…
  • from
  • $4500
    monthly

 

Atlantic Breeze- 3 Bedroom Family Vacation Home with Loft! Pet…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This home is great for families! It has been recently updated with new tile throughout, new furnishings and bedding, and…
  • from
  • $3700
    monthly

 

BARBADOS ISLE- 3 Bedroom Family Vacation Home with large deck…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Ready for some fun in the sun? This Ramrod Key vacation home is the perfect spot! This home is located…
  • from
  • $3000
    monthly

 

CASA TURQUESA- 3 Bedroom Oceanfront Family Vacation Home directly on…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water…
  • from
  • $6000
    monthly

 

Cruikshank- 3 Bedroom Oceanfront Vacation Home with Spacious Decks and…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Enjoy many peaceful days and evenings at Cruikshank Isle, situated right on the tip of Cruikshank Island on Summerland Key…
  • from
  • $4800
    monthly

 

Dolphin Beach- Luxury 3 Bedroom Oceanfront Family Vacation Beach House!…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Gorgeous luxury open oceanfront home on Summerland Beach. This expansive 3 bedroom, 2 bath home is just perfect for large…
  • from
  • $7000
    monthly

 

Fifty-Eight Palms- 2 Bedroom Waterfront Vacation Home with Large Heated…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • A tropical paradise awaits you at Fifty-Eight Palms. Located on Big Pine in the Port Pine Heights area. This vacation…
  • from
  • $3800
    monthly

 

Flying Could- 2 Bedroom Pet Friendly Vacation Home with Open…

  • 2 Bedrooms, 1 Bathroom, Sleeps 4
  • Fishing, swimming, boating.... Whatever your pleasure, the protective 75' seawall and clear, clean deepwater boating canal offers excellent choices! Relax…
  • from
  • $2750
    monthly

 

Lafitte Landing- Quaint 2 Bedroom Canal Front Vacation Rental Home…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Lafitte Landing is the perfect destination for your Florida Keys vacation. Very nicely appointed 2 bedroom, 2 bathroom canal front…
  • from
  • $2700
    monthly

 

Margarita Villa- 3 Bedroom Waterfront Pet Friendly Vacation Home -…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best…
  • from
  • $4500
    monthly

 

Owl's Nest- 3 Bedroom Bayview Vacation Home with Boat Dock!…

  • 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

 

Sunset Bay- Spacious Oceanfront 2 Bedroom Vacation Rental Home! Florida…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • This is a WEEKLY RENTAL! Welcome to Sunset Bay, where you’ll experience the most glorious sunsets! Located on tranquil Big…
  • from
  • $1750
    weekly

 

Tobago Hideaway- 3 Bedroom Pet Friendly Family Vacation Home! Florida…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Ready for that Florida Keys vacation? We are ready for you! Adorable ground level home with 3 bedrooms and 2…
  • from
  • $2300
    monthly

 

Spacious 3 Bedroom Pet Friendly Vacation Home with Boat Dock!…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Come and enjoy the wonderful Florida Keys lifestyle at Tropical Bay. Located at mile marker 22, close to Key West…
  • from
  • $2200
    monthly

 

Breeze Swept- Waterfront 3 Bedroom Vacation Home with Heated Pool!…

  • 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

 

Bow Channel Manor - Oceanfront 3 Bedroom Family Vacation Home…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Welcome to Bow Channel Manor and step back in time to Old Florida! You'll find this plantation style home reminiscent…
  • from
  • $5200
    monthly

 

2 Bedroom Pet Friendly Vacation Home with Pool - Blue…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation…
  • from
  • $5600
    monthly

 

3 Bedroom Vacation Rental Home- Suncatcher's Dream Florida Keys

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Relax and enjoy this light and tropical, like-new vacation home with a private heated swimming pool. Step onto the large…
  • from
  • $4500
    monthly

 

Islamorada 1 Bedroom Bayfront Vacation Rental Condo - The Palms…

  • 1 Bedroom, 2 Bathrooms, Sleeps 2
  • Minimum Rental: 28 days. Everything in this unit is new - furnishings, linens, kitchen, appliances, and bath rooms. Great views…
  • from
  • $1900
    monthly

 

The Palms #309

  • 2 Bedrooms, 2 Bathrooms, Sleeps 5
  • MINIMUM STAY: 29 DAYS Exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the…
  • from
  • $2000
    monthly

 

Charming 3 Bedroom Family Vacation Home - Steps to Beach…

  • 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
  • $3990
    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

 

2 Bedroom First Floor Vacation Duplex on Florida Bay -…

  • 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
  • $2500
    weekly

 

Florida Bay 2 Bedroom Vacation Duplex - Sleeps 6- LITTLE…

  • 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
  • $2500
    weekly

 

Oceanview 5th Floor 2 Bedroom Vacation Rental Condo - BEACON…

  • 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

 

Private 1 Bedroom Waterfront Vacation Rental - 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
  • $1040
    weekly

 

Oceanview 2 Bedroom Vacation Condo Rental - Private Balcony -…

  • 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
  • $3500
    monthly

 
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