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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Highland City holiday rentals

Outdoor pool, pool umbrellas, pool loungers

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is 2.081.255 ₫
2.331.005 ₫ total
includes taxes & fees
5 May - 6 May
Lake Ida Beach Resort
House (3 Bedrooms) | Interior

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
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 4.504.995 ₫
11.545.960 ₫ total
includes taxes & fees
7 May - 8 May
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Great communication with host. "
United States
Reid
The price is 1.567.527 ₫
6.565.174 ₫ total
includes taxes & fees
1 May - 2 May
BlockHaven near Legoland & Disney
Lobby

Elita Inn

Elita Inn
3.0 star property
Dundee
7.4 out of 10, Good, (29 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is 2.107.920 ₫
2.360.871 ₫ total
includes taxes & fees
29 May - 30 May
Elita Inn
House (4 Bedrooms) | Interior

Legoland & Lakes Pool Home Pet Friendly

Legoland & Lakes Pool Home Pet Friendly
3.0 star property
Winter Haven
The price is 5.163.620 ₫
15.532.222 ₫ total
includes taxes & fees
1 May - 2 May
Legoland & Lakes Pool Home Pet Friendly
House (3 Bedrooms) | Interior

Explore & Relax: Chic & Cozy Retreat in Lakeland!

Explore & Relax: Chic & Cozy Retreat in Lakeland!
3.0 star property
Lakeland
10.0 out of 10, Exceptional, (1 review)
"We had a great time. The house was beautiful. Decor was beautiful and bedding comforting. I sleep so good. The house was family friendly and plenty of rooms. "
United States
Debra
The price is 6.454.525 ₫
14.270.560 ₫ total
includes taxes & fees
4 May - 5 May
Explore & Relax: Chic & Cozy Retreat in Lakeland!
House (2 Bedrooms) | Interior

Dog-friendly Yard! Walkable Dixieland District Gem

Dog-friendly Yard! Walkable Dixieland District Gem
2.0 star property
Dixieland
The price is 2.581.810 ₫
7.226.170 ₫ total
includes taxes & fees
12 May - 13 May
Dog-friendly Yard! Walkable Dixieland District Gem
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

Birch Hill Suites - Lakeland

Birch Hill Suites - Lakeland

2/10 Terrible
"I was not able to stay because I had a family emergency. I tried to contact the hotel about refund but as time we’re on, I forgot about it so I never stayed at the location when I pulled up to the location. It was so many people outside hanging outside. I didn’t feel safe."
jennifer 1-night trip
Posted 8 hours ago
Birch Hill Suites - Lakeland

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. Sanlan Bird and Wildlife Sanctuary and The Club at Eaglebrooke 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.