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Highland City Holiday Rentals

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Check prices for these dates

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

Our top choices for Highland City holiday 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
The price is S$292
includes taxes & fees
12 Nov - 13 Nov
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
The price is S$99
includes taxes & fees
8 Dec - 9 Dec
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
The price is S$357
includes taxes & fees
15 Nov - 16 Nov
Walkable Dixieland District Gem With Yard
A modern reception area with a wooden panel design, a tiled floor, and a white door in the background.

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 S$110
includes taxes & fees
18 Nov - 19 Nov
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
The price is S$859
includes taxes & fees
21 Nov - 22 Nov
10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
A silver Tesla Model 3 parked in a driveway with a white fence and trees in the background.

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 S$449
includes taxes & fees
9 Nov - 10 Nov
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
The price is S$453
includes taxes & fees
8 Nov - 9 Nov
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
The price is S$550
includes taxes & fees
1 Dec - 2 Dec
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

Comfort Inn & Suites Lakeland North I-4

Comfort Inn & Suites Lakeland North I-4

8/10 Good
"It was ok"
Moneka 1-night trip
Posted less than an hour ago
Comfort Inn & Suites Lakeland North I-4

Frequently asked questions

Can I find a holiday rental in Highland City?

Yes, we offer holiday rentals where you'll be just 11.5 mi (18.5 km) from LEGOLAND® Florida, providing a more remote option if you want a quiet place to stay.

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 wider area.

What’s a holiday rental in Highland City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland City. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family gatherings.