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1,064 listings
  • $40,998
    fair price
    $140 below market
    • 15,586 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from VA to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Virginia Beach, VA / 912 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/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH4PS029125
    Stock: 27565370
    Certified Pre-Owned: No

  • $36,998
    fair price
    $906 below market
    • 11,972 miles
    • No accidents, 2 owners, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from NJ to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Mays Landing, NJ / 1,109 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: 5TDGZRBH5MS154590
    Stock: 27379412
    Certified Pre-Owned: No

  • New Listing
    $36,590
    great price
    $4,301 below market
    • 30,318 miles
    • 1 accident, 1 owner, corporate fleet 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 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: 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: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH7PS029380
    Stock: 2003794309
    Certified Pre-Owned: No
    Listed since: 06-26-2025

  • New Listing
    $46,998
    good price
    $917 below market
    • 12,006 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from NC to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Asheville, NC / 759 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/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH7RS530111
    Stock: 26950630
    Certified Pre-Owned: No

  • $38,998
    good price
    $1,890 below market
    • 27,934 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from OR to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Beaverton, OR / 2,692 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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDDZRBH8NS224295
    Stock: 27076464
    Certified Pre-Owned: No

  • Price Drop
    $38,990
    good price
    $2,170 below market
    • 49,591 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 20 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Oklahoma City, OK / 1,204 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: 5TDFZRBH1NS187180
    Stock: 2003725614
    Certified Pre-Owned: No
    Listed since: 05-15-2025

  • Price Drop
    $43,998
    fair price
    $1,097 below market
    • 10,073 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 22 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from NV to FL*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Las Vegas, NV / 2,139 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: 5TDKDRAH7RS523712
    Stock: 27403861
    Certified Pre-Owned: No

    • 34,765 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Corpus Christi, TX / 1,005 miles away from Key West, FL

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

    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: 5TDGZRAH3NS141372
    Stock: NS141372T
    Certified Pre-Owned: No

  • $29,998
    fair price
    $294 above market
    • 22,674 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 8 Seats, 19 City / 26 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from SC to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    Close

    Located in Charleston, SC / 578 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: Yes

    Features and Specs:

    22 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 5TDBZRFH5KS717526
    Stock: 27095250
    Certified Pre-Owned: No

  • Price Drop
    $29,998
    great price
    $4,074 below market
    • 56,305 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Clearwater, FL*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Clearwater, FL / 239 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: 5TDHZRAHXNS547704
    Stock: 27519195
    Certified Pre-Owned: No

  • $26,704
    good price
    $1,271 below market
    • 69,857 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 20 City / 26 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Knoxville, TN / 795 miles away from Key West, FL

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

    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: 5TDJZRFH2KS592626
    Stock: KS592626P
    Certified Pre-Owned: No

  • Price Drop
    $43,888
    fair price
    $61 above market
    • 16,695 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Kennewick, WA / 2,547 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:

    24 Combined MPG (21 City/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH3RS574056
    Stock: RS574056T
    Certified Pre-Owned: No

  • $42,998
    fair price
    $716 below market
    • 14,919 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from OR to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Beaverton, OR / 2,692 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/28 Highway)

    Listing Information:

    VIN: 5TDKDRBH0PS021023
    Stock: 27271383
    Certified Pre-Owned: No

  • New Listing
    • 66,678 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 21 City / 29 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in San Antonio, TX / 1,101 miles away from Key West, FL

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

    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: 5TDGZRAH1NS100478
    Stock: NS100478P
    Certified Pre-Owned: No

  • New Listing
    $37,998
    fair price
    $806 below market
    • 10,390 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 22 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Fort Myers, FL*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Fort Myers, FL / 141 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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH7PS013356
    Stock: 27488708
    Certified Pre-Owned: No

  • Price Drop
    $40,590
    good price
    $3,460 below market
    • 20,674 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Tampa, FL / 238 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: 5TDKDRAH4RS532514
    Stock: 2003684676
    Certified Pre-Owned: No
    Listed since: 05-28-2025

  • $34,998
    fair price
    $691 below market
    • 12,187 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 22 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from IL to FL*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Schaumburg, IL / 1,261 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: 5TDKDRAH4PS510252
    Stock: 27436425
    Certified Pre-Owned: No

  • $39,477
    fair price
    $732 below market
    • 26,407 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Minneapolis, MN / 1,552 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,Heated Seats,Keyless S...

    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: 5TDKDRBH6PS504788
    Stock: PS504788A
    Certified Pre-Owned: No

  • $16,799
    fair price
    $442 below market
    • 131,254 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 19 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

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

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Leather Seats,Navi...

    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: 5TDKKRFH6FS093309
    Stock: SO93309A
    Certified Pre-Owned: No

  • $7,990
    fair price
    $1,019 below market
    • 122,192 miles
    • 4 accidents, 3 owners, personal use only
    • 7 Seats, 16 City / 22 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Heated seats
    • Leather Seats
    • Sunroof/Moonroof
    • Third-row seating
    Close

    Located in Springfield, VA / 1,018 miles away from Key West, FL

    Low Mileage,Rare Find,3rd Row Seat,Brake Assist,Heated Seats,Leather Seats,Premium Sound,Sunroof / Moonroof,V6 Cylinder Engine,5-Speed A/T,Heated Seat...

    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:

    19 Combined MPG (16 City/22 Highway)

    Listing Information:

    VIN: JTEEP21A370209632
    Stock: 24898P
    Certified Pre-Owned: No

  • New Listing
    $38,998
    fair price
    $700 below market
    • 13,047 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 22 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from CA to FL*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Palmdale, CA / 2,279 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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH6PS523200
    Stock: 27585851
    Certified Pre-Owned: No

Showing 106 - 126 out of 1,064 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.