Unplugged Weekend - Vacation Rentals in Key West

Fleming-O From US $583
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Opal Key Resort & Marina, Key West From US $432
         

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9.2 (1081 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Key West

Over 5018+ Luxury Places to Stay in or Near Key West

Top-Rated Vacation Rentals with a Pool in Key West

Over 3670+ Top-Rated Vacation Rentals with a Pool in or Near Key West
Almond Tree Inn Hotel - Adults Only From US $279
         

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10.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath From US $874
         

Pet-Friendly Vacation Rentals in Key West

Over 1542+ Pet-Friendly Vacation Rentals in or Near Key West
Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury 3-Bedroom Waterfront Home with Pool AND Dock! From US $1,331
         

9.8 (138 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
PET FRIENDLY! Completely REMODELED! 3 Bedroom 3 bathroom home. Sleeps 8 From US $625
         

See More Pet-Friendly Vacation Rentals in Key West on PetFriendly.io

Large Vacation Homes & Villas in Key West

Over 557+ Large Vacation Homes & Villas in or Near Key West
Harbor House Suite A From US $2,693
         

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10.0 (3 Reviews)
House
  • Security/Safety
  • Child Friendly
  • Internet
Conch style home in Oldtown with private pool AND dock! From US $1,183
         

3-Story spacious conch style home w/private pool & dock! From US $1,177
         

Wheelchair Accessible Vacation Homes in Key West

Over 1139+ Wheelchair Accessible Vacation Homes in or Near Key West
Point Break Suites From US $225
         

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7.3 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Weatherstation Inn From US $246
         

9.4 (1005 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Tropical Executive at The Truman Annex in Key West From US $567
         

Bermuda Retreat-waterfront 2BR 2BA condo w/pool & boat slip From US $418
         

'Oceanside Oasis' Direct Ocean Views & 3 BR'S From US $513
         

10.0 (147 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Panoramic Ocean: Beach from every window From US $615
         

9.8 (336 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Key West Vacation Rentals and Airbnb Places to Stay Under $200

Over 304+ Key West Vacation Rentals and Airbnb Places to Stay Under $200
Hilton Garden Inn Key West/The Keys Collection From US $190
         

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8.0 (1232 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Alhambra at The Truman Annex in Key West From US $146
         

8.6 (63 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
A Pleasant Stay at The Truman Annex in Key West From US $173
         

Instantly Bookable Vacation Homes in Key West

Over 3245+ Instantly Bookable Vacation Homes in or Near Key West
Parking, Heated Pool, Pet Friendly - Seagate House From US $1,797
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Key West Vacation Rentals

With more than 365 Key West vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Unpluggedweekend 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 Unpluggedweekend 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 955.97 ft² on average, with prices averaging US $825 a night.

Unpluggedweekend 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 114
Resorts 46
Holiday Apartments 43
Hotels 4
Cottages 2
B&B 1
Villas 1

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

Pro Tip: Unpluggedweekend makes it easy to compare the best listings on Unpluggedweekend homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Unpluggedweekend 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 81°F       Low 67°F
March - May
High 87°F       Low 70°F
June - August
High 91°F       Low 80°F
September - November
High 90°F       Low 73°F

Key West Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Key West?
How many vacation rentals are available in Key West?

Currently, the total number of properties listed in 2026 is over 365 in the Key West area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Key West.