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Highland City Vacation Rentals

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Our top choices for Highland City vacation rentals

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
The price is CA $58
CA $320 total
includes taxes & fees
Nov 12 - Nov 13
BlockHaven near Legoland & Disney

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
The price is CA $93
CA $104 total
includes taxes & fees
Nov 24 - Nov 25
Lake Ida Beach Resort

3. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is CA $177
CA $390 total
includes taxes & fees
Nov 11 - Nov 12
Walkable Dixieland District Gem With Yard

4. Elita Inn

Elita Inn
3.0 star property
Dundee
7.2 out of 10, Good, (39 reviews)
"Great p"
United States
Gilles
The price is CA $107
CA $120 total
includes taxes & fees
Nov 10 - Nov 11
Elita Inn

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
The price is CA $704
CA $946 total
includes taxes & fees
Nov 9 - Nov 10
10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney

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
The price is CA $182
CA $492 total
includes taxes & fees
Nov 11 - Nov 12
Lakefront Retreat on Lake Ariana w/ EV Charger

7. Modern Dundee Townhome Near Lakes & Legoland!

Modern Dundee Townhome Near Lakes & Legoland!
3.5 star property
Dundee
The price is CA $185
CA $495 total
includes taxes & fees
Nov 8 - Nov 9
Modern Dundee Townhome Near Lakes & Legoland!

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

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is CA $237
CA $601 total
includes taxes & fees
Dec 1 - Dec 2
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

Find out more about Highland City

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Highland City. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.