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Highlands County Vacations & Trips from $257

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Your Highlands County Vacation

Embark on your next epic adventure with a Highlands County vacation package, and leave knowing the finer details are taken care of. Plus with the ability to customize your getaway, it'll be one you won't forget. Not sure where to stay? Sebring is among the leading cities to visit during a trip to Highlands County. Expedia has hotels, flights and whatever else you need to help you put together your very own customized Highlands County vacation today.

Top destinations in Highlands County

An aerial view of a city intersection with multiple roads converging at a central roundabout, surrounded by buildings and greenery.
FlightsHotels

Sebring

Sebring

The Latest Highlands County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with a large bed, bedside tables, a desk, and a window with curtains.
    Jan 11 - Jan 15

    Quality Inn Fort Myers Cape Coral + Flight

    Fort Myers
    4 nights
    2.0 star property
    7.6/10 - Good (514 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $389
    $257
    per traveler
    found 1 day ago
    Quality Inn Fort Myers Cape Coral
  • A resort with a central pool, multiple lounge areas, and a beach view.
    Jan 11 - Jan 15

    Tween Waters Island Resort & Spa + Flight

    Captiva
    4 nights
    3.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "This is a great property,"
    Reviewed November 2, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $908
    $571
    per traveler
    found 1 day ago
    Tween Waters Island Resort & Spa
  • A breakfast buffet setup with a variety of food items and a seating area.
    Jan 23 - Jan 28

    Hawthorn Extended Stay by Wyndham Naples + Flight

    Naples
    5 nights
    3.0 star property
    9.0/10 - Wonderful (1,001 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - RSW • Nonstop PGD - PSM • Nonstop
    Save 100% on your flight
    $839
    $541
    per traveler
    found 1 day ago
    Hawthorn Extended Stay by Wyndham Naples
  • A balcony with a view of a beach, a table, and chairs.
    Dec 17 - Dec 21

    Windward Passage Resort + Flight

    Fort Myers Beach
    4 nights
    2.0 star property
    8.6/10 - Excellent (23 reviews)
    "Location is amazing, being right on the beach. Having access to beach chairs to take down to the beach and return is a major plus. Gas grills on the property also give you the opportunity to grill up some dinner and watch the sunset while eating on your balcony!! I would definitely recommend!"
    Reviewed October 31, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop RSW - BOS • Nonstop
    Save 100% on your flight
    $1,251
    $832
    per traveler
    found 1 day ago
    Windward Passage Resort
  • A balcony with a TV, a chair, and a view of a beach with a pier.
    Jan 11 - Jan 15

    Edison Beach House + Flight

    Fort Myers Beach
    4 nights
    3.5 star property
    9.4/10 - Exceptional (1,959 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $915
    $623
    per traveler
    found 1 day ago
    Edison Beach House

Discover the most popular places to visit in Highlands County

Seagulls flying against a blue sky with clouds.
Photo by Nancy Morrissey
Open Photo by Nancy Morrissey

Lake Jackson

9.2/10 (57 reviews)
Commune with nature and explore the great outdoors at Lake Jackson during your travels in Sebring. Stroll along the area's lakeside, or simply savor its top-notch restaurants.
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Highlands County Hotel Deals

A Holiday Inn Express hotel with a modern facade, large windows, and a well-lit entrance.

Holiday Inn Express & Suites Lake Placid by IHG

Holiday Inn Express & Suites Lake Placid by IHG
2.5 star property
13.8 mi from Highlands County
9.2 out of 10, Wonderful, (871 reviews)
$153 nightly
The price is $173
Nov 8 - Nov 9
Total with taxes and fees
Holiday Inn Express & Suites Lake Placid by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.