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Highland City Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Highland City vacation rentals

A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

1. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (8 reviews)
"Very nice house for a small family! Close to everything!"
United States
Yuliett
$211 nightly
The price is $237
Nov 12 - Nov 13
Total with taxes and fees
BlockHaven near Legoland & Disney
A swimming pool with a fence, lounge chairs, and a palm tree.

2. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (198 reviews)
"Clean room and private area loved it"
United States
Heather
$70 nightly
The price is $79
Nov 22 - Nov 23
Total with taxes and fees
Lake Ida Beach Resort
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

3. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
$248 nightly
The price is $278
Nov 9 - Nov 10
Total with taxes and fees
Walkable Dixieland District Gem With Yard
A bedroom with a bed, a nightstand, and a wooden floor.

4. Elita Inn

Elita Inn
3.0 star property
Dundee
7.2 out of 10, Good, (38 reviews)
"Very nice accommadations..friendly staff"
United States
lance
$75 nightly
The price is $84
Nov 6 - Nov 7
Total with taxes and fees
Elita Inn
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with a sink and stools.

5. 10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney

10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
2.0 star property
Winter Haven
$587 nightly
The price is $644
Nov 6 - Nov 7
Total with taxes and fees
10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

6. Lakefront Retreat on Lake Ariana w/ EV Charger

Lakefront Retreat on Lake Ariana w/ EV Charger
3.0 star property
Auburndale
8.0 out of 10, Very good, (1 review)
"This house has beautiful views of Lake Ariana and you can walk to old town and access the lake easily. The house is an old classic central Florida house with some quirks, but had room for family and entertaining. Auburndale beautiful and was a great place to visit and had quick access to highways. "
United States
Katrina
$314 nightly
The price is $351
Nov 9 - Nov 10
Total with taxes and fees
Lakefront Retreat on Lake Ariana w/ EV Charger
A modern kitchen with white cabinetry, granite countertops, stainless steel appliances, and a wooden floor.

7. Modern Dundee Townhome Near Lakes & Legoland!

Modern Dundee Townhome Near Lakes & Legoland!
3.5 star property
Dundee
$316 nightly
The price is $353
Nov 8 - Nov 9
Total with taxes and fees
Modern Dundee Townhome Near Lakes & Legoland!
A modern kitchen with a central island, bar stools, pendant lighting, and stainless steel appliances.

8. Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
$383 nightly
The price is $429
Dec 1 - Dec 2
Total with taxes and fees
Golf, Dine & Unwind Poolside! Haines City Getaway
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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Top Highland City Hotel Reviews

Hampton Inn by Hilton Plant City

Hampton Inn by Hilton Plant City

10/10 Excellent
"Ive stayed here two times now. Beds and pillows are great. Staff is super friendly. The breakfast is better then other fancy hotels I’ve stayed at."
Jazmin 1-night trip
Posted 13 hours ago
Hampton Inn by Hilton Plant City

Find out more about Highland City

Everything you need to know about Highland City vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland City vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland City vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland City vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland City. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland City in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland City rentals

At Expedia, we put the best Highland City vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland City vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Highland City?

Yes, we have vacation rentals where you'll be just 11.5 mi (18.5 km) from LEGOLAND® Florida, offering you a more secluded option if you want a quiet place to stay.

What are some of the best vacation rentals that Highland City has to offer?

Great quiet and comfortable, South Central Lakeland location.: This vacation home rental outside of Highland City is located on a lake and offers an outdoor pool, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

What’s there to see and do in Highland City?

Explore the area and family-friendly sights such as LEGOLAND® Florida, or get out into nature at a spot like The Circle B Bar Reserve. The Club at Eaglebrooke and Mary Holland Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Highland City like?

Vacation rentals are private properties you can book for a long or short time in Highland City. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip.