Highland City Vacation Rentals

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Our top choices for Highland City vacation rentals

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 CA $102
CA $114 total
includes taxes & fees
Apr 30 - May 1
Lake Ida Beach Resort

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 CA $233
CA $597 total
includes taxes & fees
May 7 - May 8
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

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 CA $81
CA $341 total
includes taxes & fees
May 1 - May 2
BlockHaven near Legoland & Disney

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 CA $109
CA $123 total
includes taxes & fees
May 28 - May 29
Elita Inn

Legoland & Lakes Pool Home Pet Friendly

Legoland & Lakes Pool Home Pet Friendly
3.0 star property
Winter Haven
The price is CA $268
CA $807 total
includes taxes & fees
Apr 30 - May 1
Legoland & Lakes Pool Home Pet Friendly

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 CA $334
CA $719 total
includes taxes & fees
May 4 - May 5
Explore & Relax: Chic & Cozy Retreat in Lakeland!

Dog-friendly Yard! Walkable Dixieland District Gem

Dog-friendly Yard! Walkable Dixieland District Gem
2.0 star property
Dixieland
The price is CA $134
CA $375 total
includes taxes & fees
May 11 - May 12
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

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?

Midway between Disney and the Gulf beaches: This vacation home rental outside of Highland City offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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 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.