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1,063 listings
  • $39,300
    good price
    $2,260 below market
    • 12,661 miles
    • No accidents, 1 owner, personal use
    • 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 Madison, WI / 1,349 miles away from Key West, FL

    CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Sea...

    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: 5TDKDRBH3PS025938
    Stock: PS025938K
    Certified Pre-Owned: No

  • $35,990
    great price
    $5,755 below market
    • 26,947 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: 5TDKDRAH9RS530922
    Stock: 2003455916
    Certified Pre-Owned: No
    Listed since: 02-03-2025

  • Price Drop
    $39,590
    good price
    $2,501 below market
    • 29,429 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 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: 5TDKDRAH9RS532735
    Stock: 2003810102
    Certified Pre-Owned: No
    Listed since: 06-10-2025

  • $38,990
    great price
    $7,152 below market
    • 24,279 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    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: 5TDKDRBH2RS531344
    Stock: 2003647215
    Certified Pre-Owned: No
    Listed since: 04-22-2025

  • Price Drop
    $36,998
    good price
    $2,220 below market
    • 19,242 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 27 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from OH to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Columbus, OH / 1,073 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: 5TDHZRBH0NS226687
    Stock: 27326497
    Certified Pre-Owned: No

  • Price Drop
    $37,590
    great price
    $7,323 below market
    • 28,778 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 21 City / 28 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • 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: 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: 5TDKDRBH0RS531651
    Stock: 2003666147
    Certified Pre-Owned: No
    Listed since: 05-07-2025

  • Price Drop
    $22,500
    great price
    $2,499 below market
    • 82,797 miles
    • 3 accidents, 1 owner, personal use only
    • 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 Farmington Hills, MI / 1,240 miles away from Key West, FL

    3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Leather Seats,Navigation System,S...

    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: 5TDJZRFH0JS529801
    Stock: JS529801P
    Certified Pre-Owned: No

  • Price Drop
    $28,000
    great price
    $2,757 below market
    • 38,570 miles
    • No accidents, 2 owners, personal use
    • 8 Seats, 20 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Union, NJ / 1,195 miles away from Key West, FL

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

    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: 5TDBZRBH4MS526494
    Stock: MS526494T
    Certified Pre-Owned: No

  • Price Drop
    $37,590
    great price
    $4,409 below market
    • 25,600 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 Buffalo, NY / 1,274 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: 5TDKDRAHXRS537698
    Stock: 2003579428
    Certified Pre-Owned: No
    Listed since: 03-14-2025

  • Price Drop
    $37,590
    great price
    $4,687 below market
    • 28,735 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 Los Angeles, CA / 2,281 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: 5TDKDRAH6RS531350
    Stock: 2003700727
    Certified Pre-Owned: No
    Listed since: 05-10-2025

  • New Listing
    $19,890
    great price
    $3,070 below market
    • 82,592 miles
    • 8 Seats, 20 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 Wesley Chapel, FL / 254 miles away from Key West, FL

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

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    23 Combined MPG (20 City/27 Highway)

    Listing Information:

    VIN: 5TDZZRFH4KS358474
    Stock: M358474P
    Certified Pre-Owned: No

  • Price Drop
    $21,377
    great price
    $2,536 below market
    • 90,781 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Third-row seating
    • Blind Spot Monitorin...
    Close

    Located in Lexington, KY / 941 miles away from Key West, FL

    3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,Lane Keeping Assist,Satellite Radio,V6 Cylinder Engine,Power Door Locks,Satellite Radio,Brake Assis...

    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: 5TDBZRFH4KS974290
    Stock: KS974290P
    Certified Pre-Owned: No

  • Price Drop
    $36,590
    great price
    $4,823 below market
    • 28,730 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 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: 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: 5TDKDRAH6RS528867
    Stock: 2003512387
    Certified Pre-Owned: No
    Listed since: 02-25-2025

  • Price Drop
    $34,405
    great price
    $3,883 below market
    • 52,567 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 Freehold, NJ / 1,168 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: 5TDKDRBH4PS030856
    Stock: FTP7267
    Certified Pre-Owned: No

  • $32,500
    great price
    $3,719 below market
    • 68,062 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 20 City / 27 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Lexington, KY / 941 miles away from Key West, FL

    3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heated Steering Wheel,Keyless Sta...

    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: 5TDFZRBH6MS093293
    Stock: MS093293P
    Certified Pre-Owned: No

  • Price Drop
    $37,590
    good price
    $4,320 below market
    • 30,103 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 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: 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: 5TDKDRAH1RS528906
    Stock: 2003602037
    Certified Pre-Owned: No
    Listed since: 03-31-2025

  • Price Drop
    $38,590
    good price
    $3,238 below market
    • 26,503 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 Los Angeles, CA / 2,281 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: 5TDKDRAH6RS532451
    Stock: 2003442437
    Certified Pre-Owned: No
    Listed since: 05-16-2025

  • Price Drop
    $36,990
    great price
    $3,453 below market
    • 34,131 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: 5TDKDRAH2RS537906
    Stock: 2003701260
    Certified Pre-Owned: No
    Listed since: 05-15-2025

  • Price Drop
    $29,998
    great price
    $4,523 below market
    • 51,122 miles
    • No accidents, 2 owners, rental vehicle
    • 7 Seats, 21 City / 29 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Tampa, FL*
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    • Third-row seating
    Close

    Located in Tampa, FL / 247 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:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 5TDGZRAH0NS128465
    Stock: 27462692
    Certified Pre-Owned: No

  • Price Drop
    $36,590
    good price
    $4,387 below market
    • 33,579 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 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: 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: 5TDKDRAH1RS532518
    Stock: 2003602020
    Certified Pre-Owned: No
    Listed since: 04-04-2025

  • Price Drop
    $18,054
    great price
    $3,400 below market
    • 108,915 miles
    • 1 accident, 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 Old Bridge, NJ / 1,175 miles away from Key West, FL

    CarFax 1-Owner,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Heated Seats,Keyless Start,Leather Seats,Navigation...

    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: 5TDDKRFH1GS304281
    Stock: SB130678A
    Certified Pre-Owned: No

Showing 22 - 42 out of 1,063 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.