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

W. Plaza de Lago - Beautiful 2 Bedroom Waterfront Vacation…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 5
  • MINIMUM STAY: 28 DAYS NEW LISTING - Available this winter! But Hurry… this home promises to be a favorite. Beautifully…
  • from
  • $4000
    monthly

 

MOON BAY A410 - Fourth Floor 2 Bedroom Waterfront Vacation…

  • 2 Bedrooms, 1 Bathroom, Sleeps 4
  • MINIMUM STAY: 7 NIGHTS. This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers…
  • from
  • $925
    weekly

 

KEY LARGO YACHT CLUB #8 - 3 Story Vacation Townhouse…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Minimum Rental: 1 Month Exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring…
  • from
  • $3500
    monthly

 

Manatee Manor - Waterfront 3 Bedroom Luxury Single Family Vacation…

  • 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
  • MINIMUM STAY: 28 DAYS NEW OPPORTUNITY to LIVE THE LIFE! This 3 Bedrooms and 2 ½ Baths home with POOL,…
  • from
  • $5500
    monthly

 

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
  • $6000
    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
  • $2000
    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
  • $2900
    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
  • $5400
    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
  • $2600
    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
  • $3600
    weekly

 

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
  • $3000
    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
  • $2900
    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
  • $3300
    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
  • $3550
    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
  • $8000
    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
  • $5000
    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
  • $1100
    weekly

 

Oceanfront 2 bedroom Vacation Rental Condo - 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
  • $4400
    monthly

 

Islamorada 2 Bedroom Oceanfront Vacation Rental Condo - The Palms…

  • 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
  • $2200
    monthly

 

Canal front 3 Bedroom Family Vacation Home with Dockage -…

  • 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

 

Oceanfront 2 Bedroom Vacation Condo Rental -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
  • $2400
    monthly

 

Waters Edge 2 Bedroom end unit townhouse vacation rental Brock…

  • 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
  • $1500
    weekly

 

Fishing at your Doorstep - 2 Bedroom Vacation Rental -Moon…

  • 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
  • $990
    weekly

 

Oceanside 3 Bedroom Family Vacation Beach House -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

 

Pet Friendly 3 Bedroom Family Beach House Vacation Rental -My…

  • 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

 

Pet Friendly 4 Bedroom Vacation Home | Easy Beach Access…

  • 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

 

Beacon Reef #310 - 2 Bedroom Vacation Condo on the…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: ONE MONTH. NEW ON THE RENTAL MARKET - Beacon Reef is one of the most desirable condominium complexes…
  • from
  • $3200
    monthly

 

Furnished 3 Bedroom Bayfront Family Vacation Home with Private Pool-CASA…

  • 3 Bedrooms, 3.5 Bathrooms, Sleeps 10
  • Casa Dorado is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in…
  • from
  • $6000
    weekly

 

Waterfront 4 Bedroom Vacation Home with Private Pool - Lyons…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • MINIMUM STAY: 29 DAYS Lyons Landing is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and…
  • from
  • $6500
    monthly

 

Gorgeous 3 Bedroom Vacation Home on the Bay - Gulfview…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 29 DAYS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family…
  • from
  • $7500
    monthly

 

4 Bedroom single family home with Private Pool - PLANTATION…

  • 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
  • $6500
    monthly

 

2 Bedroom Single Family Vacation Home Rental - 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
  • $3500
    monthly

 

Brand New Vacation Home for the Perfect Keys Vacation- Bayside…

  • 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
  • $3600
    monthly

 

Gorgeous 2 Bedroom Vacation Condo - Completely Remodeled- The Palms…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM STAY: 30 DAYS A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been…
  • from
  • $3000
    monthly

 

Tavernier 3 Bedroom Canalfront Vacation Home with Heated Pool -…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY 29 DAYS. JANUARY SPECIAL - $500 RENT DISCOUNT - BOOK NOW! BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED…
  • from
  • $4400
    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
  • $5400
    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
  • $2500
    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
  • $6000
    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
  • $1900
    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
  • $3750
    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
  • $2575
    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
  • $4200
    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
  • $3000
    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
  • $3100
    monthly

 

Newly Remodeled 2 Bedroom Vacation Condo Rental -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
  • $2400
    monthly

 

Oceanview 2 bedroom Vacation Condo Rental - 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
  • $2000
    monthly

 

Located Directly on the Beach

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: 28 Nights Located DIRECTLY on the beach you will love this updated beach front home with all new…
  • from
  • $4500
    monthly

 

Casa Kai Key Largo 4 Bedroom Oceanview Vacation Home

  • 4 Bedrooms, 2 Bathrooms, Sleeps 10
  • MINIMUM STAY: 1 MONTH Water views from almost every room in this home! Gaze at the water from your bedroom,…
  • from
  • $4500
    monthly

 

Oceanfront 2 Bedroom Vacation Condo Rental - The Palms 301

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 28 DAYS. This exceptional condo has been impeccably maintained and is located in one of the finest condo…
  • from
  • $2200
    monthly

 
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