Search Resort Hotels in Highland City

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Highland City Resorts

Tropical Paradise Rental in Key West-Inspired Gated Resort
Fridge, microwave, oven, stovetop

Tropical Paradise Rental in Key West-Inspired Gated Resort

10.0 out of 10, Exceptional, (4)
"Awesome stay and Great Host!"
Tropical Paradise Rental in Key West-Inspired Gated Resort
Charming 3BR Retreat w/ Pool, Resort Perks & Easy Access to Orlando Attractions
A heated pool

Charming 3BR Retreat w/ Pool, Resort Perks & Easy Access to Orlando Attractions

Charming 3BR Retreat w/ Pool, Resort Perks & Easy Access to Orlando Attractions
Epic Lakeside Resort – 2 Homes on 2 Acres with 800' of Waterfront
Private kitchen

Epic Lakeside Resort – 2 Homes on 2 Acres with 800' of Waterfront

Epic Lakeside Resort – 2 Homes on 2 Acres with 800' of Waterfront
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland City Hotel Reviews

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

10/10 Excellent
"Great location if you plan to go to Legoland/Peppa Pig park. It was very clean and breakfast was great"
Anelis 1-night trip
Posted 14 hours ago
Best Western Plus Winter Haven Inn & Suites