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

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

 

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

 

The Palms #316

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit…
  • from
  • $3500
    monthly

 

Angelfish Cove- 3 Bedroom Waterfront Vacation Home with Private Pool…

  • 3 Bedrooms, 2.5 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
    monthly

 

PLANTATION BY THE SEA 121

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 28 DAYS. Enjoy this beautifully remodeled two bedroom condo at Plantation by the Sea. Brand new kitchen (12/2010)…
  • from
  • $1900
    monthly

 

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
  • $2000
    monthly

 

LITTLE BAY COTTAGE

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • MINIMUM RENTAL: 3 NIGHTS. This is one of three rental units on this property. The cottage is a ground level…
  • from
  • $350
    nightly

 

Key Colony Beach Tropical Pool Home w/Private Beach Access

  • 3 Bedrooms, 2 Bathrooms, Sleeps 9
  • We purchased this pool home in Key Colony Beach at the end of May 2010. It is spacious and private…
  • from
  • $2200
    weekly

 

Largo Kai Upper Levels

  • 4 Bedrooms, 4.1 Bathrooms, Sleeps 8
  • MINIMUM STAY: 1 MONTH Looking for a spacious ocean front home but don't need a mansion? The upper two floors…
  • from
  • Contact Owner

 

Casa Lorelane

  • 7 Bedrooms, 5 Bathrooms, Sleeps 24
  • This home is for the guests who expect extraordinary accommodations. Plan your dream vacation now to The Florida Keys and…
  • from
  • Contact Owner

 

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

 

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

 

Largo Kai

  • 5 Bedrooms, 6.1 Bathrooms, Sleeps 10
  • MINIMUM STAY: 28 DAYS Expansive ocean views are yours from almost every room in this magnificent ocean front home. This…
  • from
  • Contact Owner

 

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

 

Sunset Serenity

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • MINIMUM STAY: 29 DAYS. Enjoy the tranquil setting of this single family home located directly on the Florida Bay. Walk…
  • from
  • $5500
    monthly

 

Beacon Reef 306

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • MINIMUM STAY: 28 DAYS. Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two…
  • from
  • $4000
    monthly

 

The Palms #417

  • 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
  • $1800
    monthly

 
Quick Search

How2 Travel Deals

Super Savers The latest Newsletter