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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Highland City holiday rentals

Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

1. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (6 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
The price is 1.544.839 ₫
6.480.432 ₫ total
includes taxes & fees
27 Sept - 28 Sept
BlockHaven near Legoland & Disney
House (3 Bedrooms) | Interior

2. Modern Lakeland Golf Retreat w/ Putting Green

Modern Lakeland Golf Retreat w/ Putting Green
3.0 star property
Lake Hollingsworth
10.0 out of 10, Exceptional, (1 review)
The price is 4.683.240 ₫
10.913.510 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Modern Lakeland Golf Retreat w/ Putting Green
Outdoor pool, pool umbrellas, pool loungers

3. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (196 reviews)
"Clean room and private area loved it"
United States
Heather
The price is 1.849.880 ₫
2.071.865 ₫ total
includes taxes & fees
23 Sept - 24 Sept
Lake Ida Beach Resort
Lobby

4. Elita Inn

Elita Inn
3.0 star property
Dundee
7.6 out of 10, Good, (34 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is 2.107.458 ₫
2.360.353 ₫ total
includes taxes & fees
23 Sept - 24 Sept
Elita Inn
House (2 Bedrooms) | Interior

5. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is 3.278.268 ₫
7.236.386 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Walkable Dixieland District Gem With Yard
House (3 Bedrooms) | Interior

6. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Florence Villa
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is 4.292.970 ₫
10.511.792 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Hook, Line & Leisure: Lakefront Gem w/ Porch!
House (3 Bedrooms) | Interior

7. 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 2.992.070 ₫
8.698.078 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Lakefront Retreat on Lake Ariana w/ EV Charger
House (4 Bedrooms) | Interior

8. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
3.0 star property
Winter Haven
The price is 3.798.920 ₫
13.167.421 ₫ total
includes taxes & fees
25 Sept - 26 Sept
Legoland & Lakes Pool Home w/ Private Suite
Apartment (3 Bedrooms) | Interior

9. Modern Dundee Townhome Near Lakes & Legoland!

Modern Dundee Townhome Near Lakes & Legoland!
3.5 star property
Dundee
The price is 3.434.376 ₫
9.193.460 ₫ total
includes taxes & fees
23 Sept - 24 Sept
Modern Dundee Townhome Near Lakes & Legoland!
Apartment (0 Bedroom) | Interior

10. Hot Tub & Fire Pit: Lakefront Home on Lake Eloise

Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
3.5 star property
Winter Haven
The price is 5.177.980 ₫
11.146.708 ₫ total
includes taxes & fees
8 Oct - 9 Oct
Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
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

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

10/10 Excellent
"Large clean modern room, very nice toiletries. The breakfast was great, a different hot option each day."
Krystal 2-night trip
Posted 1 hour ago
Best Western Plus Winter Haven Inn & Suites 

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 Southgate Shopping Center 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.