Florida Rental Vacations - Vacation Rentals in Florida Keys

Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Florida Keys

Over 10000+ Luxury Places to Stay in or Near Florida Keys
Little Bay Compound From US $16,123
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Sunset Harbor Resort Key West Florida From US $11,249
         

New
Resort
  • Air Conditioner
  • Pool
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Florida Keys

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Florida Keys
Almond Tree Inn Hotel - Adults Only From US $438
         

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10.0 (1005 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Florida Keys

Over 4390+ Pet-Friendly Vacation Rentals in or Near Florida Keys
Sunshine Key King Travel Trailer 4 From US $238
         

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8.9 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Atlantic View Luxury Villa with Pool From US $1,097
         

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10.0 (2 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Pool
Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp From US $1,049
         

10.0 (81 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures From US $626
         

Luxury 3-Bedroom Waterfront Home with Pool AND Dock! From US $1,423
         

9.8 (138 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
PET FRIENDLY! Completely REMODELED! 3 Bedroom 3 bathroom home. Sleeps 8 From US $665
         

Large Vacation Homes & Villas in Florida Keys

Over 2351+ Large Vacation Homes & Villas in or Near Florida Keys
Pelico Paradise From US $304
         

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9.6 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Islands of Islamorada From US $954
         

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9.8 (72 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,350
         

Conch style home in Oldtown with private pool AND dock! From US $1,336
         

Wheelchair Accessible Vacation Homes in Florida Keys

Over 2984+ Wheelchair Accessible Vacation Homes in or Near Florida Keys
Weatherstation Inn From US $413
         

9.4 (1004 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ From US $530
         

10.0 (162 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Birds Eye Loft Perched Above the Marina 1BR 1BA 5413 From US $298
         

Top Floor unit with a ocean view! PRIVATELY OWNED From US $275
         

9.8 (134 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Florida Keys Vacation Rentals and Airbnb Places to Stay Under $200

Over 1199+ Florida Keys Vacation Rentals and Airbnb Places to Stay Under $200
Dolphin Retreat From US $162
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterside Suites & Marina From US $171
         

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9.0 (1276 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Luxurious Tropical Retreat with Private Tiki Hut From US $119
         

9.8 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Oyster's Pearl at The Truman Annex in Key West From US $168
         

9.4 (61 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Florida Keys

Over 9170+ Instantly Bookable Vacation Homes in or Near Florida Keys
Parking, Heated Pool, Pet Friendly - Seagate House From US $1,797
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lagoon View Retreat 2 Kings Pickleball Marina From US $499
         

9.8 (155 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Beautiful Kawama Townhouse From US $638
         

9.8 (145 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

About Florida Keys Vacation Rentals

With more than 14608 Florida Keys vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Floridarentalvacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Florida Keys.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Floridarentalvacations Florida Keys, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Florida Keys. Places to stay near Florida Keys are 830.99 ft² on average, with prices averaging $642 a night.

Floridarentalvacations makes it easy and safe to find and compare vacation rentals in Florida Keys with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Florida Keys

Type Count
Vacation Homes 8872
Holiday Apartments 1283
Hotels with Suites 850
Resorts 515
Villas 383
Cottages 288
B&B 53
Others 33
Cabin Rentals 25
Hostels 3
Ski Chalet Rentals 2

Use these Quick Filters to Find a Vacation Rental in Florida Keys

Pro Tip: Floridarentalvacations makes it easy to compare the best listings on Floridarentalvacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Floridarentalvacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Florida Keys.

Weather in Florida Keys

View the weather forecast for Florida Keys before booking your Florida Keys Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Florida Keys Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Florida Keys?
How many vacation rentals are available in Florida Keys?

Currently, the total number of properties listed in 2026 is over 14608 in the Florida Keys area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Florida Keys.