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1,041 listings
  • New Listing
    $38,998
    fair price
    $508 above market
    • 23,902 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from OK to FL*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Oklahoma City, OK / 1,208 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDLZRAH3NS105129
    Stock: 27179029
    Certified Pre-Owned: No

  • Price Drop
    $18,539
    good price
    $1,061 below market
    • 117,354 miles
    • 3 accidents, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Wexford, PA / 1,114 miles away from Key West, FL

    CarFax 1-Owner,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Leather Seats,Navigation System,Satellite Radio,Sunroof /...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDJKRFH5GS290937
    Stock: V290937A
    Certified Pre-Owned: No

  • New Listing
    $17,998
    good price
    $197 below market
    • 125,389 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 21 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from WA to FL*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Lynnwood, WA / 2,727 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: Yes

    Features and Specs:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDZZRFH5HS234402
    Stock: 27092197
    Certified Pre-Owned: No

  • New Listing
    $23,998
    good price
    $1,387 below market
    • 66,994 miles
    • 2 accidents, 1 owner, personal use only
    • 7 Seats, 19 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Daytona Beach, FL*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Daytona Beach, FL / 322 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    21 Combined MPG (19 City/25 Highway)

    Listing Information:

    VIN: 5TDYKRFH9GS125097
    Stock: 27260699
    Certified Pre-Owned: No

  • New Listing
    $18,998
    fair price
    $308 below market
    • 79,774 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 19 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from CA to FL*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Costa Mesa, CA / 2,259 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    21 Combined MPG (19 City/25 Highway)

    Listing Information:

    VIN: 5TDZKRFH6FS056727
    Stock: 27087806
    Certified Pre-Owned: No

  • New Listing
    • 95,705 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 19 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to FL*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Pharr, TX / 1,031 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    21 Combined MPG (19 City/25 Highway)

    Listing Information:

    VIN: 5TDKKRFH0FS092155
    Stock: 27578005
    Certified Pre-Owned: No

  • $29,998
    fair price
    $1,502 below market
    • 40,352 miles
    • 2 accidents, 2 owners, rental vehicle
    • 8 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from GA to FL*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Lithia Springs, GA / 660 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: Yes

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDZZRAH5NS548229
    Stock: 27606738
    Certified Pre-Owned: No

  • $39,590
    good price
    $1,501 below market
    • 30,339 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Sacramento, CA / 2,503 miles away from Key West, FL

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH5RS532652
    Stock: 2003775355
    Certified Pre-Owned: No
    Listed since: 06-13-2025

  • $26,685
    good price
    $1,781 below market
    • 80,727 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Los Angeles, CA / 2,282 miles away from Key West, FL

    CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping A...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDHZRAH8LS015798
    Stock: V5548660-1
    Certified Pre-Owned: No

  • $36,998
    fair price
    $709 above market
    • 25,946 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Naples, FL*
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Naples, FL / 110 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: Yes

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDYZRAH5MS516472
    Stock: 27241878
    Certified Pre-Owned: No

  • Price Drop
    $28,899
    fair price
    $547 below market
    • 48,415 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 8 Seats, 21 City / 29 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Thousand Oaks, CA / 2,314 miles away from Key West, FL

    CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Kee...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDZZRAH4NS104971
    Stock: NS104971P
    Certified Pre-Owned: No

  • New Listing
    $27,998
    good price
    $1,597 below market
    • 44,070 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Orlando, FL*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Orlando, FL / 271 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: No

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDCZRAH6MS521061
    Stock: 27464124
    Certified Pre-Owned: No

  • New Listing
    • 113,435 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Austin, TX / 1,055 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDDKRFH9GS255427
    Stock: 27671140
    Certified Pre-Owned: No

  • New Listing
    • 92,890 miles
    • No accidents, 3 owners, rental vehicle
    • 8 Seats, 21 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to FL*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Irving, TX / 1,079 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDZZRFH7JS239820
    Stock: 27298826
    Certified Pre-Owned: No

    • 26,695 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 22 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from AZ to FL*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Tolleson, AZ / 1,935 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: Yes

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH1PS041573
    Stock: 27450995
    Certified Pre-Owned: No

  • $44,233
    fair price
    $722 above market
    • 27,425 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Helena, MT / 2,264 miles away from Key West, FL

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free L...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDFZRBH5NS226515
    Stock: NS226515T
    Certified Pre-Owned: No

  • $32,498
    good price
    $1,867 below market
    • 39,845 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • AutoNation Toyota Weston (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Davie, FL / 136 miles away from Key West, FL

    Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler50 State EmissionsBlack; Softex Seat TrimCelestial Silver MetallicThis v...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDGZRAH9NS140212
    Stock: NS140212
    Certified Pre-Owned: No
    Listed since: 03-22-2025

  • New Listing
    $22,998
    fair price
    $291 above market
    • 89,379 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 8 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from GA to FL*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Buford, GA / 671 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: No

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDZZRFH8KS299266
    Stock: 27101544
    Certified Pre-Owned: No

  • New Listing
    • 89,368 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to FL*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in McKinney, TX / 1,079 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDZZRFH2KS366587
    Stock: 27473855
    Certified Pre-Owned: No

    • 29,572 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Dallas, TX / 1,072 miles away from Key West, FL

    At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...

    AutoCheck Vehicle History Summary

    Accident Free Vehicle: Yes

    Personal Use Only: Yes

    History Provider: AutoCheck

    Title Details: Clean Title

    Salvage Vehicle: No

    Frame Damage: No

    Theft History: No

    Lemon Status: No

    Free History Report: No

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDCZRBH6NS183001
    Stock: 2003772374
    Certified Pre-Owned: No
    Listed since: 06-06-2025

  • New Listing
    • 119,517 miles
    • 8 Seats, 20 City / 24 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to FL*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in San Antonio, TX / 1,088 miles away from Key West, FL

    CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    22 Combined MPG (20 City/24 Highway)

    Listing Information:

    VIN: 5TDZARFH6KS043442
    Stock: 27559595
    Certified Pre-Owned: No

Showing 316 - 336 out of 1,041 listings

Buying a Toyota Highlander in Key West Florida

For those exploring the vibrant surroundings of Key West, Florida, the Toyota Highlander presents a compelling option. Its comfortable and quiet ride makes long trips to local attractions like the Ernest Hemingway Home and Museum or the beautiful beaches a pleasurable experience. The elevated visibility offered by the Highlander can enhance your journey through the scenic streets and coastal views of the island. Additionally, the strong V6 engine provides a balance of good power and fuel economy, making it suitable for both leisurely drives and more spirited excursions around the southernmost point of the continental U.S.

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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.