Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Highland Park vacation rentals

Interior

Cottage in Avon Park

This old Florida feeling getaway is 420 friendly and a great place to just relax
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay at Kellie’s farm, the property is big and has a big pond or little lake at the back, the scenery looks like you’re somewhere in the wild side of Montana and feels like a grizzly bear can come out of the trees at any moment! Haha but it’s very safe, nothing to worry about. The farm has chickens, pigs, a calf, dogs, etc. if you love animals you will love this place for sure! We would definitely come back and we 100% recommend this place."
United States
Steve M.
The price is ￥12,102
￥23,008 total
includes taxes & fees
Jan 31 - Feb 1
This old Florida feeling getaway is 420 friendly and a great place to just relax
Lobby

Aparthotel in Dundee

Elita Inn
3.0 star property
8.0 out of 10, Very Good, (19 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is ￥12,650
￥14,167 total
includes taxes & fees
Feb 18 - Feb 19
Elita Inn
Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

Vacation Home in Winter Haven

BlockHaven near Legoland & Disney
3.5 star property
10.0 out of 10, Exceptional, (1 review)
"House was great, perfect central location. Very quiet neighborhood nice farm outside peaceful back yard seating area. "
United States
Wade
The price is ￥10,753
￥40,910 total
includes taxes & fees
Feb 12 - Feb 13
BlockHaven near Legoland & Disney
Lake

Cabin in Lake Wales

Camp Mack Lodge, Marina & RV Resort
3.0 star property
9.0 out of 10, Wonderful, (193 reviews)
"Nice rooms helpful staff would go again for sure"
United States
David
Camp Mack Lodge, Marina & RV Resort
Exterior detail

Apartment in Winter Haven

Tiny Paradise
9.4 out of 10, Exceptional, (8 reviews)
"I have stayed on property a few times, first experience with tiny Paradise very quaint and clean enjoyed my stay."
United States
SUSAN
The price is ￥9,966
￥19,641 total
includes taxes & fees
Jan 21 - Jan 22
Tiny Paradise
Outdoor pool, pool umbrellas, sun loungers

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is ￥11,859
￥13,282 total
includes taxes & fees
Jan 31 - Feb 1
Lake Ida Beach Resort
1 bedroom, WiFi, bed sheets

Cabin in Lake Alfred

The Lake Alfred Citrus Wood Guest Cabin
9.6 out of 10, Exceptional, (37 reviews)
"Great place!"
United States
Michael A.
The price is ￥14,095
￥18,951 total
includes taxes & fees
Feb 1 - Feb 2
The Lake Alfred Citrus Wood Guest Cabin
1 bedroom, bed sheets

Apartment in Lake Alfred

THE SIGNATURE ORANGE GROVE SUITE
9.4 out of 10, Exceptional, (9 reviews)
"Room was super clean Had a fridge with drinks and snacks which most places do not have Owners were very friendly and ready to help with anything you need"
United States
Dave J.
The price is ￥11,385
￥15,914 total
includes taxes & fees
Jan 27 - Jan 28
THE SIGNATURE ORANGE GROVE SUITE
Fridge, microwave, oven, stovetop

Cottage in Lake Hamilton

Luxury Cottage Near Legoland & Chain of Lakes
10.0 out of 10, Exceptional, (6 reviews)
"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."
United States
Dallas C.
The price is ￥15,812
￥32,541 total
includes taxes & fees
Jan 22 - Jan 23
Luxury Cottage Near Legoland & Chain of Lakes
TV, fireplace

Vacation Home in Winter Haven

Spacious 4-bedroom house in pleasant Winter Haven with AC
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"An outstanding stay! The house was extremely clean, welcoming, and had all the amenities that made our family vacation unforgettable in our visit to Legoland park"
Mexico
Monica
The price is ￥14,547
￥56,771 total
includes taxes & fees
Jan 27 - Jan 28
Spacious 4-bedroom house in pleasant Winter Haven with AC
TV

Cottage in Winter Haven

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is ￥18,184
￥43,918 total
includes taxes & fees
Jan 21 - Jan 22
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Smart TV, fireplace, printers

Vacation Home in Winter Haven

Modern Comfort, Pet Friendly, 2 King Beds
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "
United States
Kristofer G.
The price is ￥13,960
￥35,210 total
includes taxes & fees
Jan 21 - Jan 22
Modern Comfort, Pet Friendly, 2 King Beds
Interior

Vacation Home in Winter Haven

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Yes the dogs liked it and they enjoyed walking in the neighborhood."
United States
John W.
The price is ￥13,915
￥25,831 total
includes taxes & fees
Jan 24 - Jan 25
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Room

Condo in Lake Wales

Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
10.0 out of 10, Exceptional, (1 review)
"Had an amazing stay! Property was exactly how it was described- clean, comfortable, very safe. (As a solo woman traveling alone feeling safe always makes a trip easier) The bed and sheets were sooo comfortable! Micki was kind, attentive, incredibly responsive and happily accommodated me, making my entire experience was seamless. I felt right at home, would happily return. 5 Stars is not enough to describe how wonderful Micki is as host!"
United States
Anonymous traveler
The price is ￥17,924
￥23,237 total
includes taxes & fees
Jan 27 - Jan 28
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
Outdoor pool, a heated pool

Vacation Home in Kissimmee

Resort Villa, Pools Fun and relaxation/w Kingbed
9.2 out of 10, Wonderful, (29 reviews)
"This host was very nice, accomodating and responsive. Great communication."
United States
yolanda t.
The price is ￥17,401
￥45,274 total
includes taxes & fees
Feb 14 - Feb 15
Resort Villa, Pools Fun and relaxation/w Kingbed
Outdoor dining

Apartment in Winter Haven

⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
10.0 out of 10, Exceptional, (3 reviews)
"The place was clean and tidy, accessible to a lot of stores and attractions in the surrounding area, and the hosts were SO nice and easy to contact throughout our stay-even checking in on us to make sure everything was going good. Would totally stay again!"
United States
Kaitlyn F.
The price is ￥16,365
￥21,493 total
includes taxes & fees
Jan 25 - Jan 26
⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
Property grounds

Vacation Home in Lake Alfred

Cozy house in peaceful Lake Alfred with AC, WiFi very secluded.
2.0 star property
8.4 out of 10, Very Good, (18 reviews)
"So cute! Right on the water, peaceful and quiet. Had all the basics we needed."
United States
Rebecca
The price is ￥11,385
￥27,425 total
includes taxes & fees
Jan 31 - Feb 1
Cozy house in peaceful Lake Alfred with AC, WiFi very secluded.
Fridge, microwave, oven, stovetop

Vacation Home in Kissimmee

King bd / Modern Home sleeps 8 w/ private backyard
8.6 out of 10, Excellent, (4 reviews)
"Very nice stay and very clean. Beds were super comfortable and the living space was cozy. Our host was accomodating and communicative wnd check in was as smooth as could be. Absolutely worth it."
United States
Jon W.
The price is ￥14,436
￥50,797 total
includes taxes & fees
Jan 21 - Jan 22
King bd / Modern Home sleeps 8 w/ private backyard
Interior

Apartment in Winter Haven

The Unique cozy studio
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Cool little place, love the outdoor private patio.Very close to everything downtown"
United States
Cory M.
The price is ￥12,655
￥28,949 total
includes taxes & fees
Jan 21 - Jan 22
The Unique cozy studio
Paper towels

Vacation Home in Winter Haven

Private/Spacious 1BR Central Near LegoLand 2 Miles
9.6 out of 10, Exceptional, (8 reviews)
"Location was great. Internet was great. Bed was good. Cleaned and comfortable.."
United States
Maria
The price is ￥12,808
￥27,248 total
includes taxes & fees
Jan 27 - Jan 28
Private/Spacious 1BR Central Near LegoLand 2 Miles
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 Park Hotel Reviews

Hampton Inn Winter Haven

Hampton Inn Winter Haven

10/10 Excellent
"Nice "
Lia 1-night trip
Posted 17 hours ago
Hampton Inn Winter Haven

Find out more about Highland Park

Search for holiday rentals in Highland Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Park using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Highland Park?

Yes, there are vacation rentals where you'll be just 11.9 mi (19.1 km) from LEGOLAND® Florida, offering you a secluded option to escape the hustle and bustle. Highland Park is known for its restaurants.

What's the top vacation rental in Highland Park?

Charming 7-Bedroom Estate with AC & Resort-Style Pool – Winter Haven: Visitors like this Highland Park vacation home rental. It offers an outdoor pool, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You and your friends and family can relax into your vacation with amenities like a garden.

What’s there to see and do in Highland Park?

Explore the area and family-friendly sights such as LEGOLAND® Florida, or get out into nature at a spot like Lake Easy. In the larger area, you’ll find Lake Wailes and Grand Hotel.

What’s a vacation rental in Highland Park like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Highland Park. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.