Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Cabins
Condos
Cottages
Estates
Hotels
Homes
Boats
Studios
Townhomes
Villas
Yachts
Barns
Bungalows
Castles
Chalets
Farmhouses
Lodges

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Welcome to the new VacationRentals.com! Use the new filters and search options to find your next vacation rental.

Key West Vacation Rentals(386)

386 Results
Special Offer! High Season Discounts for 5 Star November 29 - April 30
3 - 5 night minimum stay
(24)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 night minimum stay
(12)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
    See details
    4 night minimum stay
    (27)
    • 4 BR,
    • 3 BA,
    • 1 HF BA,
    • Sleeps 12
      See details
      4 night minimum stay
      (6)
      • 6 BR,
      • 6 BA,
      • 2 HF BA,
      • Sleeps 16
        See details
        7 night minimum stay
        (41)
        • 3 BR,
        • 2 BA,
        • Sleeps 10
          Book it Now
          7 night minimum stay
          2 Reviews
          • 3 BR,
          • 2 BA,
          • Sleeps 6
          4 night minimum stay
          1 Review
          • 9 BR,
          • 7 BA,
          • 1 HF BA,
          • Sleeps 24
            See details
            6 - 7 night minimum stay
            (14)
            • 3 BR,
            • 2 BA,
            • Sleeps 6
            28 night minimum stay
            • 3 BR,
            • 2 BA,
            • 1 HF BA,
            • Sleeps 6
              See details
              28 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 6
                See details
                28 night minimum stay
                • 3 BR,
                • 2 BA,
                • Sleeps 6
                  See details
                  6 - 7 night minimum stay
                  (10)
                  • 4 BR,
                  • 4 BA,
                  • Sleeps 8
                  Special Offer! Fantasy Fest dates available! September 22 - October 22
                  Special Offer! SPEND THANKSGIVING, CHRISTMAS AND NEW YEAR'S EVE IN KEY WEST November 2 - December 31
                  3 - 4 night minimum stay
                  • 1 BR,
                  • 1 BA,
                  • Sleeps 2
                  3 - 4 night minimum stay
                  • 1 BR,
                  • 1 BA,
                  • Sleeps 4
                  7 night minimum stay
                  2 Reviews
                  • 4 BR,
                  • 1 BA,
                  • 1 HF BA,
                  • Sleeps 8
                  • 4 BR,
                  • 4 BA,
                  • Sleeps 8
                  28 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 4
                    See details
                    Special Offer! Reduced rates from the end of Oct. thru beginning of Dec. October 24 - December 10
                    • 1 BR,
                    • 1 BA,
                    • Sleeps 2
                    (24)
                    • 1 BR,
                    • 1 BA,
                    • Sleeps 4
                    From $278
                    per night
                    (36)
                    • 1 BR,
                    • 1 BA,
                    • Sleeps 4
                    (37)
                    • 1 BR,
                    • 1 BA,
                    • Sleeps 4
                    (15)
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 4
                    $250
                    per night
                    3 night minimum stay
                    (40)
                    • 2 BR,
                    • 2 BA,
                    • 1 HF BA,
                    • Sleeps 6
                    (65)
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 4
                    7 night minimum stay
                    (13)
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 4
                    (10)
                    • 5 BR,
                    • 4 BA,
                    • Sleeps 12
                    Advertisement