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1,006 listings
  • New Listing
    $26,990
    fair price
    $410 below market
    • 51,216 miles
    • 8 Seats, 19 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    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 Unavailable.

    Features and Specs:

    22 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 5TDBZRFH3KS720022
    Stock: 2003813309
    Certified Pre-Owned: No
    Listed since: 06-12-2025

  • New Listing
    $43,981
    fair price
    $378 above market
    • 28,121 miles
    • No accidents, 1 owner, rental vehicle
    • 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 Freehold, NJ / 1,168 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: 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: 5TDKDRBH3RS544006
    Stock: FTP7379
    Certified Pre-Owned: No

  • Price Drop
    $38,440
    good price
    $1,081 below market
    • 15,217 miles
    • 2 accidents, 1 owner, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Old Bridge, NJ / 1,175 miles away from Key West, FL

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

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBHXNS580166
    Stock: AHP9494
    Certified Pre-Owned: No

  • Price Drop
    $35,990
    fair price
    $411 above market
    • 48,990 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 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 Chesapeake, VA / 904 miles away from Key West, FL

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

    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: 5TDKDRAH8PS001801
    Stock: PS001801P
    Certified Pre-Owned: No

  • $30,777
    fair price
    $463 below market
    • 52,933 miles
    • 1 accident, 1 owner, rental vehicle
    • 8 Seats, 22 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 Farmington Hills, MI / 1,240 miles away from Key West, FL

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

    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: 5TDKDRAH9PS016839
    Stock: PS016839P
    Certified Pre-Owned: No

  • New Listing
    $34,998
    fair price
    $662 above market
    • 16,677 miles
    • 2 accidents, 2 owners, corporate fleet vehicle
    • 8 Seats, 22 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from DE to FL*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Newark, DE / 1,102 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: No

    Features and Specs:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH7PS019125
    Stock: 27473547
    Certified Pre-Owned: No

  • $39,999
    fair price
    $35 above market
    • 46,500 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 22 City / 29 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in San Leandro, CA / 2,533 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: 5TDKDRAH1PS037247
    Stock: 8F2V40
    Certified Pre-Owned: No
    Listed since: 06-04-2025

  • New Listing
    $39,998
    fair price
    $504 above market
    • 17,188 miles
    • 1 accident, 1 owner, personal use
    • 7 Seats, 21 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 Irvine, CA / 2,248 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: 5TDJZRAH5NS118469
    Stock: 27453169
    Certified Pre-Owned: No

  • New Listing
    • 55,909 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH1KS355209
    Stock: 2003816274
    Certified Pre-Owned: No
    Listed since: 06-12-2025

  • New Listing
    $31,497
    fair price
    $731 below market
    • 46,890 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 20 City / 27 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Montclair, CA / 2,249 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: 5TDBZRBH9NS586109
    Stock: 7V7FWD
    Certified Pre-Owned: No
    Listed since: 04-24-2025

    • 32,033 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 21 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 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: 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: 5TDGZRAH3NS091914
    Stock: 2003735999
    Certified Pre-Owned: No
    Listed since: 05-28-2025

    • 105,311 miles
    • 1 accident, 2 owners, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Rockwall, TX / 1,061 miles away from Key West, FL

    Rare Find,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Entertainment System,Heated Seats,Keyless Start,Lane Keeping Assist,Le...

    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/26 Highway)

    Listing Information:

    VIN: 5TDJZRFH0JS886007
    Stock: JS886007A
    Certified Pre-Owned: No

  • $33,938
    fair price
    $731 below market
    • 65,506 miles
    • 1 accident, 1 owner, rental vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Clovis, CA / 2,390 miles away from Key West, FL

    3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Brake Assist,Heated Seats,Lane Keeping Assist,Remote Start,Satellite Radio,Sunroof / Moon...

    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDGZRBHXNS162119
    Stock: NS162119PR
    Certified Pre-Owned: No

  • New Listing
    $36,998
    fair price
    $276 below market
    • 18,674 miles
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Melbourne, FL*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Melbourne, FL / 250 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:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDHZRAH2NS132991
    Stock: 27307816
    Certified Pre-Owned: No

  • $38,590
    good price
    $1,485 below market
    • 36,391 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 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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH3RS534531
    Stock: 2003833166
    Certified Pre-Owned: No
    Listed since: 06-21-2025

    • 37,597 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • AutoNation Honda Hollywood (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Hollywood, FL / 140 miles away from Key West, FL

    The following items have been reconditioned on this vehicle: all new tires! Sun/Moonroof3rd Row SeatSpecial ColorLane Keeping AssistKeyless Sta...

    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: 5TDGZRAH1MS075726
    Stock: MS075726
    Certified Pre-Owned: No
    Listed since: 04-13-2025

  • Price Drop
    $30,998
    good price
    $1,234 below market
    • 41,308 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 22 City / 29 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    • Upgraded Headlights
    Close

    Located in Albuquerque, NM / 1,656 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:

    25 Combined MPG (22 City/29 Highway)

    Listing Information:

    VIN: 5TDKDRAH9PS016565
    Stock: 7W5C2J
    Certified Pre-Owned: No
    Listed since: 03-28-2025

  • $23,990
    fair price
    $316 below market
    • 110,269 miles
    • No accidents, 1 owner, personal use only
    • 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 Chicago, IL / 1,269 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: 5TDJZRFH6KS610061
    Stock: 2003831711
    Certified Pre-Owned: No
    Listed since: 06-19-2025

  • Price Drop
    $32,590
    fair price
    $11 below market
    • 52,097 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
    • Navigation
    • Sunroof/Moonroof
    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: 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: 5TDHZRBH8LS015282
    Stock: 2003787053
    Certified Pre-Owned: No
    Listed since: 06-12-2025

  • Price Drop
    $33,645
    good price
    $1,963 below market
    • 47,385 miles
    • No accidents, 1 owner, rental vehicle
    • 8 Seats, 22 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 Spoiler2Nd Row Bench Seat50 State EmissionsBlack; Softex Seat TrimCelestial Silve...

    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: 5TDKDRAH4PS040403
    Stock: PS040403
    Certified Pre-Owned: No
    Listed since: 05-21-2025

  • $18,985
    great price
    $2,999 below market
    • 85,471 miles
    • 1 accident, 2 owners, personal use
    • 8 Seats, 20 City / 24 Hwy MPG
    • AutoNation Chevrolet Pembroke Pines (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Pembroke Pines, FL / 137 miles away from Key West, FL

    3rd Row SeatLane Keeping AssistRear Spoiler50 State EmissionsAsh; Fabric Seat TrimPredawn Gray MicaThis vehicle includes a Money-Back Guarante...

    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: 5TDZARFH7KS044261
    Stock: KS044261
    Certified Pre-Owned: No
    Listed since: 06-23-2025

Showing 421 - 441 out of 1,006 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.