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965 listings
  • New Listing
    • 124,323 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from NC to FL*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Gastonia, NC / 741 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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH6HS520454
    Stock: 27208449
    Certified Pre-Owned: No

    • 72,494 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 18 City / 24 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDBKRFH1GS228925
    Stock: 2003780201
    Certified Pre-Owned: No
    Listed since: 06-03-2025

  • Price Drop
    • 94,005 miles
    • No accidents, 2 owners, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Power Driver Seat
    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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDBZRFH6JS813549
    Stock: 2003814512
    Certified Pre-Owned: No
    Listed since: 06-23-2025

    • 30,316 miles
    • No accidents, 1 owner, personal use
    • 8 Seats, 21 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Blind Spot Monitorin...
    • Power Driver Seat
    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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDZZRFHXKS289502
    Stock: 2003878168
    Certified Pre-Owned: No
    Listed since: 07-18-2025

  • New Listing
    • 26,942 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 Baltimore, MD / 1,069 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: 5TDGZRBH7NS163955
    Stock: 2003862549
    Certified Pre-Owned: No
    Listed since: 07-11-2025

    • 104,940 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Kansas City, MO / 1,252 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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDDKRFH0FS081486
    Stock: 2003756401
    Certified Pre-Owned: No
    Listed since: 07-11-2025

    • 112,132 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
    • Third-row seating
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Indianapolis, IN / 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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDZZRFH0JS246026
    Stock: 2003681094
    Certified Pre-Owned: No
    Listed since: 05-03-2025

    • 100,799 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 19 City / 25 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Atlanta, GA / 658 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: Yes

    Features and Specs:

    21 Combined MPG (19 City/25 Highway)

    Listing Information:

    VIN: 5TDYKRFH3FS119973
    Stock: 2003689117
    Certified Pre-Owned: No
    Listed since: 04-24-2025

  • New Listing
    • 58,801 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • 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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDYK3EH8DS115414
    Stock: 2003926193
    Certified Pre-Owned: No
    Listed since: 07-26-2025

  • Price Drop
    • 27,448 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 29 Hwy MPG
    • Miami Lakes Automall (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Miami Lakes, FL / 131 miles away from Key West, FL

    CARFAX One-Owner. Clean CARFAX. Odometer is 4665 miles below market average!Priced below KBB Fair Purchase Price! OVER 400 USED CARS IN OUR INVENTORY ...

    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: 5TDJZRAH9NS120550
    Stock: C5Q175183A
    Certified Pre-Owned: No
    Listed since: 04-20-2025

    • 28,607 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TN to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Franklin, TN / 842 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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDDZRFH8HS463795
    Stock: 27067734
    Certified Pre-Owned: No

    • 80,858 miles
    • No accidents, 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
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    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: 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: 5TDKKRFH9FS088539
    Stock: 27515738
    Certified Pre-Owned: No

    • 116,673 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TN to FL*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Murfreesboro, TN / 830 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 (21 City/27 Highway)

    Listing Information:

    VIN: 5TDKZRFH2HS521679
    Stock: 25789875
    Certified Pre-Owned: No

    • 118,575 miles
    • No accidents, 2 owners, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from VA to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    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:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDDKRFH2GS333532
    Stock: 27689543
    Certified Pre-Owned: No

  • New Listing
    • 31,928 miles
    • No accidents, 2 owners, personal use
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to FL*
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Fort Worth, TX / 1,091 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: 5TDFZRAH6MS046072
    Stock: 27139942
    Certified Pre-Owned: No

  • New Listing
    • 27,950 miles
    • No accidents, 1 owner, rental vehicle
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Proximity Key For Do...
    • Towing Equipment -in...
    • Cruise Control w/Ste...
    • LCA/Lane Tracing Ass...
    • Curtain 1st 2nd And...
    Close

    Located in Woburn, MA / 1,380 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:

    Listing Information:

    VIN: 5TDKDRBH8PS045313
    Stock: 8F32K2
    Certified Pre-Owned: No
    Listed since: 05-27-2025

    • 100,869 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 21 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in San Diego, CA / 2,204 miles away from Key West, FL

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,Lane Keeping Assist,V6 Cylinder Engine,Power ...

    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: 5TDZZRFH2HS205018
    Stock: HS205018P
    Certified Pre-Owned: No

    • 88,348 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 8 Seats, 21 City / 27 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Blind Spot Monitorin...
    • Power Driver Seat
    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: 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: 5TDZZRFH1KS354754
    Stock: 2003879664
    Certified Pre-Owned: No
    Listed since: 07-18-2025

  • $39,998
    fair price
    $473 above market
    • 28,200 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from MD to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Gaithersburg, MD / 1,041 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: 5TDKDRBH1PS005557
    Stock: 27223487
    Certified Pre-Owned: No

  • New Listing
    • 30,339 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 18 City / 24 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from VA to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    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: No

    Features and Specs:

    20 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 5TDDKRFH1FS076362
    Stock: 27408972
    Certified Pre-Owned: No

  • New Listing
    • 26,877 miles
    • No 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 Roanoke, VA / 890 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:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDHZRBH0NS577728
    Stock: NS577728P
    Certified Pre-Owned: No

Showing 652 - 672 out of 965 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.