Owner Direct Vacation Rentals in Key West

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

Fairfield Inn & Suites by Marriott Key West From US $192
         

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7.5 (1100 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Porch on Frances Inn From US $337
         

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9.6 (102 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
Mirador House -Pool & Dock! From US $5,550
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bayview North One From US $2,792
         

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New
House
  • Parking
  • Pool
  • Wheelchair Accessible
AMBROSIA at Azul Mansion Key West From US $266
         

Luxury Places to Stay in Key West

Over 4764+ Luxury Places to Stay in or Near Key West
2 Sunset Harbor Resort Key West Florida
New
From US $11,498
         

New
Resort
  • Air Conditioner
  • Pool
  • Balcony/Terrace
2 Sunset Harbor Resort Key West Florida
New
From US $11,498
         

New
Resort
  • Air Conditioner
  • Pool
  • Balcony/Terrace
Lighthouse Suites Collection
New
From US $7,190
         

New
House
  • Air Conditioner
  • Parking
  • Pool
6 Bedroom 6 Bath Guesthouse on Duval Street From US $6,002
         

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9.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Key West

Over 3483+ Top-Rated Vacation Rentals with a Pool in or Near Key West
Almond Tree Inn Hotel - Adults Only From US $272
         

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

Pet-Friendly Vacation Rentals in Key West

Over 1507+ Pet-Friendly Vacation Rentals in or Near Key West
Paradise on Packer From US $233
         

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New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Fitch Lodge - Key West Historic Inns From US $353
         

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8.8 (533 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Pool
Sapphire Sabbatical From US $253
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Blue Flamingo Resort Key West From US $328
         

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8.0 (1830 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunrise Suites Panama Suite #310 From US $317
         

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7.7 (39 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Sunrise Suites Paradise Escape #407 From US $308
         

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7.5 (16 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
See More Pet-Friendly Vacation Rentals in Key West on PetFriendly.io

Large Vacation Homes & Villas in Key West

Over 542+ Large Vacation Homes & Villas in or Near Key West
Tradewinds From US $921
         

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6.8 (11 Reviews)
House
  • Pet Friendly
  • View
  • Balcony/Terrace
House with Separate Guest Cottage and Pet Friendly! From US $893
         

Waterlane House -Pool & Boat Dock From US $2,129
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Key West

Over 1113+ Wheelchair Accessible Vacation Homes in or Near Key West
Island Retreat From US $290
         

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New
House
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Silver Palms Inn From US $336
         

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9.4 (1015 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
Tarpon Watch From US $348
         

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New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
DoubleTree Resort by Hilton Grand Key - Key West From US $347
         

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8.2 (1022 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Tropical Vibes From US $515
         

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New
House
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Oceans Edge Key West Resort, Hotel & Marina From US $308
         

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9.0 (1774 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
La Te Da - Adult Only, 21 or older From US $285
         

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9.0 (152 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • View

Key West Varoom and Airbnb Places to Stay Under $200

Over 240+ Key West Varoom and Airbnb Places to Stay Under $200
Olivia Street Retreat From US $177
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Paradise Suite From US $84
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Douglas House From US $188
         

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9.6 (224 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Jewel on Jade From US $197
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
NYAH Key West - Adults Only From US $179
         

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8.0 (1004 Reviews)
House
  • Air Conditioner
  • Pool
  • TV
Hilton Garden Inn Key West/The Keys Collection From US $184
         

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7.5 (981 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Key West

Over 3083+ Instantly Bookable Vacation Homes in or Near Key West
Parking, Pool & Dock - Evershore House From US $1,725
         

9.8 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Parking, Pool & Dock - Waterlane House From US $1,667
         

9.8 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bahama Village studio @ the Galleria! From US $484
         

9.4 (16 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Parking, Pool & Waterfront - Springtide House From US $1,656
         

9.8 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront Home w/Pool & Boat Dock - Mirador House From US $2,080
         

9.6 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Key West Vacation Rentals

With more than 4773 Key West 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 Key West.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Ownerdirect Key West, 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 Key West. Places to stay near Key West are 765.41 ft² on average, with prices averaging $803 a night.

Ownerdirect makes it easy and safe to find and compare vacation rentals in Key West 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 Key West

Type Count
Vacation Homes 2383
Holiday Apartments 591
Hotels with Suites 367
Resorts 232
Cottages 116
B&B 45
Villas 45
Cabin Rentals 7
Hostels 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Key West

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 Key West.

Weather in Key West

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

December - February
High 27°C       Low 19°C
March - May
High 30°C       Low 21°C
June - August
High 32°C       Low 26°C
September - November
High 32°C       Low 22°C