Owner Direct Vacation Rentals in Florida Keys

The Best Owner Direct Vacation Rentals in Florida Keys. Explore thousands of vacation home rentals, large cabins, and villas near Florida Keys

Nauti Hideaway Ocean Pointe 2314 From US $270
         

|
10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Beach, Marina & Pickleball at Key Largo Condo!
New
From US $406
         

10.0 (8 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Ocean View Treehouse Double King Suite 3403 From US $314
         

|
10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
The Saint Martin Suite | Delightfully Updated Beach Vibes! Pool!
New
From US $560
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • Security/Safety
  • Child Friendly
Modern and Coastal Ocean Pointe 2307 From US $285
         

|
10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

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
The Greenmoor House at Lunara Bay From US $8,800
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Dreamside House at Lunara Bay From US $8,800
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Florida Keys

Over 9721+ Top-Rated Vacation Rentals with a Pool in or Near Florida Keys
Almond Tree Inn Hotel - Adults Only From US $272
         

|
10.0 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Florida Keys

Over 4251+ Pet-Friendly Vacation Rentals in or Near Florida Keys
Ocean View with Pool, 4 bedroom Vila Near Key West From US $811
         

|
10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Atlantic View Luxury Villa with Pool From US $983
         

|
10.0 (1 Review)
Villa
  • Parking
  • Pet Friendly
  • Pool
The Anchor House From US $540
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Marathon Vacation Home with Pool, Hot Tub & Movie Theater From US $421
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Downhome Cabin by the Canal From US $211
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Florida Keys

Over 2220+ Large Vacation Homes & Villas in or Near Florida Keys
The Islands of Islamorada From US $730
         

|
9.8 (69 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
411 Mariners Club From US $857
         

|
10.0 (3 Reviews)
Apartment
  • Parking
  • Pool
  • View
The Crestwood House - Private Heated Pool & Parking From US $2,969
         

|
10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Florida Keys

Over 2867+ Wheelchair Accessible Vacation Homes in or Near Florida Keys
Dream in the Keys From US $377
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Pool
  • View
Super Snapper lux w/Heated Pool, Tiki, Dock, Lanai From US $703
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
La Pirata From US $478
         

|
10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
A Wave From it All From US $375
         

|
10.0 (2 Reviews)
House
  • Air Conditioner
  • Pool
  • View

Florida Keys Varoom and Airbnb Places to Stay Under $200

Over 1188+ Florida Keys Varoom and Airbnb Places to Stay Under $200
Ocean Isles Seaside Oasis From US $190
         

|
10.0 (1 Review)
Apartment
  • Air Conditioner
  • Accessibility
  • Security/Safety
Artist House Key West From US $200
         

|
9.8 (417 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • View
Charming 2-bedroom townhome in The Landings of Largo
New
From US $196
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Casa Clara #105 From US $184
         

|
10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pool
  • View
Ocean Front Serenity Awaits From US $161
         

|
10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Florida Keys

Over 8738+ Instantly Bookable Vacation Homes in or Near Florida Keys
Waterfront Duck Key Villa From US $1,051
         

9.2 (61 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
Sunset Palms From US $165
         

New
House
  • Security/Safety
  • Child Friendly
  • Laundry
4 Bedroom Oceanview Accessible Villa
New
From US $2,886
         

New
House
  • Parking
  • Security/Safety
  • Child Friendly

About Florida Keys Vacation Rentals

With more than 13751 Florida Keys vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect 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 Ownerdirect 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 835.95 ft² on average, with prices averaging $650 a night.

Ownerdirect 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 8380
Holiday Apartments 1295
Hotels with Suites 781
Resorts 486
Villas 352
Cottages 279
B&B 54
Others 29
Cabin Rentals 24
Hostels 2
Ski Chalet Rentals 1

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

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