Surf Break Rentals - 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

Top-Rated Vacation Rentals with a Pool in Florida Keys

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Florida Keys
Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath From US $773
         

Pet-Friendly Vacation Rentals in Florida Keys

Over 4554+ 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
New The Cottage at James House From US $356
         

8.0 (2 Reviews)
Apartment
  • Pet Friendly
  • Pool
  • Balcony/Terrace
Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp From US $1,049
         

10.0 (87 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures From US $436
         

Luxury 3-Bedroom Waterfront Home with Pool AND Dock! From US $1,217
         

9.8 (142 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
PET FRIENDLY! Completely REMODELED! 3 Bedroom 3 bathroom home. Sleeps 8 From US $617
         

Large Vacation Homes & Villas in Florida Keys

Over 2371+ 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
Vista Marquesa 4/3 Ground Level Home w/Pool & 50 From US $565
         

9.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,322
         

Conch style home in Oldtown with private pool AND dock! From US $1,175
         

Wheelchair Accessible Vacation Homes in Florida Keys

Over 3054+ Wheelchair Accessible Vacation Homes in or Near Florida Keys
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ From US $335
         

10.0 (167 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Coconut Mallory Resort And Marina By Kees Vacations From US $264
         

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8.2 (834 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Top Floor unit with a ocean view! PRIVATELY OWNED From US $246
         

9.8 (142 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Affordable Key West Beach Front Condo From US $637
         

9.6 (125 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

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

Over 1353+ 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
Blue Heaven at The Truman Annex in Key West From US $192
         

9.0 (51 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Simonton Court Historic Inn & Cottages From US $168
         

9.8 (970 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Carpe' Diem Heart of the Fl. Keys Specials From US $198
         

8.8 (152 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Alhambra at The Truman Annex in Key West From US $159
         

8.6 (63 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Florida Keys

Over 9554+ 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 $436
         

9.8 (157 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Beautiful Kawama Townhouse From US $610
         

9.8 (148 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

About Florida Keys Vacation Rentals

With more than 14800 Florida Keys vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Surfbreakrentals 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 Surfbreakrentals 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 818.82 ft² on average, with prices averaging US $612 a night.

Surfbreakrentals 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 8884
Holiday Apartments 1339
Hotels 955
Resorts 513
Villas 386
Cottages 287
B&B 52
Others 40
Cabin Rentals 25
Hostels 3
Ski Chalet Rentals 2

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

Pro Tip: Surfbreakrentals makes it easy to compare the best listings on Surfbreakrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Surfbreakrentals 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 14800 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.