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1,010 listings
  • Price Drop
    $34,988
    good price
    $1,707 below market
    • 43,571 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 22 City / 29 Hwy MPG
    • Jake Sweeney Express (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Cincinnati, OH / 1,029 miles away from Key West, FL

    Jake Sweeney Is Here to Help! If you are in need of a new or used vehicle, we are offering you the ability to shop online and have your vehicle delive...

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH7PS029959
    Stock: G18421
    Certified Pre-Owned: No
    Listed since: 05-22-2025

  • Price Drop
    $35,590
    fair price
    $419 above market
    • 37,492 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Charlotte, NC / 739 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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH6PS038408
    Stock: 2003790962
    Certified Pre-Owned: No
    Listed since: 06-11-2025

  • Price Drop
    $36,998
    fair price
    $236 below market
    • 20,477 miles
    • 1 accident, 2 owners, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from CA to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Roseville, CA / 2,497 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 (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH9MS556326
    Stock: 27303363
    Certified Pre-Owned: No

  • $36,590
    fair price
    $612 below market
    • 54,456 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Charlotte, NC / 739 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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH1PS013464
    Stock: 2003802456
    Certified Pre-Owned: No
    Listed since: 06-19-2025

  • Price Drop
    $34,499
    good price
    $1,735 below market
    • 50,001 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Allentown, PA / 1,165 miles away from Key West, FL

    Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...

    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: 5TDKDRAH7PS036779
    Stock: 8GFHRL
    Certified Pre-Owned: No
    Listed since: 05-14-2025

  • New Listing
    $17,998
    fair price
    $478 above market
    • 122,783 miles
    • 1 accident, 1 owner, personal use only
    • 8 Seats, 20 City / 24 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 Puyallup, WA / 2,710 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:

    22 Combined MPG (20 City/24 Highway)

    Listing Information:

    VIN: 5TDZARFH7HS027310
    Stock: 27232068
    Certified Pre-Owned: No

    • 79,478 miles
    • No accidents, 3 owners, personal use
    • 7 Seats, 21 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Phoenix, AZ / 1,924 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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH2JS265419
    Stock: 2003714666
    Certified Pre-Owned: No
    Listed since: 05-07-2025

  • Price Drop
    $11,889
    fair price
    $953 below market
    • 121,111 miles
    • 1 accident, 1 owner, personal use only
    • 7 Seats, 20 City / 25 Hwy MPG
    • AutoNation Honda Miami Lakes (In-stock online)
    • Home delivery*
    • Third-row seating
    • Tire Pressure Warnin...
    • Rear Bench Seats
    • Stability Control
    • Aux Audio Inputs
    Close

    Located in Hialeah, FL / 131 miles away from Key West, FL

    The following items have been reconditioned on this vehicle: new brakes, all new tires and new battery! 3rd Row SeatExtra Cost PaintRear Spoiler...

    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:

    22 Combined MPG (20 City/25 Highway)

    Listing Information:

    VIN: 5TDZA3EH4CS027157
    Stock: CS027157
    Certified Pre-Owned: No
    Listed since: 04-14-2025

  • Price Drop
    $37,990
    fair price
    $202 below market
    • 32,518 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Cleveland, OH / 1,169 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: 5TDHZRBH8NS253071
    Stock: 2003838766
    Certified Pre-Owned: No
    Listed since: 06-23-2025

  • Price Drop
    $32,590
    fair price
    $456 below market
    • 40,303 miles
    • No accidents, 2 owners, personal use
    • 8 Seats, 22 City / 29 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Memphis, TN / 877 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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH3PS506404
    Stock: 2003822752
    Certified Pre-Owned: No
    Listed since: 06-18-2025

  • Price Drop
    $29,590
    fair price
    $319 above market
    • 97,724 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Cincinnati, OH / 1,017 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: 5TDGZRBH5MS526560
    Stock: 2003809018
    Certified Pre-Owned: No
    Listed since: 06-11-2025

  • Price Drop
    $30,497
    good price
    $1,726 below market
    • 64,589 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Orange, CA / 2,255 miles away from Key West, FL

    Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...

    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: 5TDGZRBH0MS083086
    Stock: 7VSFRT
    Certified Pre-Owned: No
    Listed since: 02-24-2025

  • $36,599
    good price
    $1,205 below market
    • 53,048 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Elk Grove, CA / 2,500 miles away from Key West, FL

    Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...

    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: 5TDHZRBHXNS590535
    Stock: 7VJ210
    Certified Pre-Owned: No
    Listed since: 06-23-2025

    • 31,790 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in San Antonio, TX / 1,082 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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH1RS531903
    Stock: 2003511721
    Certified Pre-Owned: No
    Listed since: 03-11-2025

  • New Listing
    $29,997
    good price
    $1,592 below market
    • 57,504 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Ventura, CA / 2,339 miles away from Key West, FL

    Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...

    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: 5TDGZRAH0MS521378
    Stock: 8CQJFR
    Certified Pre-Owned: No
    Listed since: 02-14-2025

    • 80,337 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH9KS990996
    Stock: 2003561903
    Certified Pre-Owned: No
    Listed since: 04-04-2025

  • Price Drop
    $44,998
    fair price
    $435 above market
    • 22,358 miles
    • 1 accident, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from CA to FL*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Santa Rosa, CA / 2,571 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 (20 City/27 Highway)

    Listing Information:

    VIN: 5TDFZRBH6NS208797
    Stock: 27383230
    Certified Pre-Owned: No

  • Price Drop
    $39,998
    fair price
    $1,612 below market
    • 8,181 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 22 City / 29 Hwy MPG
    • Ed Morse Sawgrass Buick Chevrolet GMC (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Sunrise, FL / 141 miles away from Key West, FL

    2024 Toyota Highlander XLE ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, He...

    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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH8RS539112
    Stock: 2SR305469B
    Certified Pre-Owned: No
    Listed since: 06-25-2025

  • New Listing
    • 48,551 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Richmond, VA / 937 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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH7KS952151
    Stock: 2003844201
    Certified Pre-Owned: No
    Listed since: 07-02-2025

  • Price Drop
    $26,990
    fair price
    $447 above market
    • 82,887 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 7 Seats, 20 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Phoenix, AZ / 1,924 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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH3KS589556
    Stock: 2003836276
    Certified Pre-Owned: No
    Listed since: 07-04-2025

  • $36,398
    fair price
    $589 below market
    • 83,986 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 28 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Memphis, TN / 880 miles away from Key West, FL

    Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...

    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/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH0PS024973
    Stock: 8GC3CQ
    Certified Pre-Owned: No
    Listed since: 06-13-2025

Showing 442 - 462 out of 1,010 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.