Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Camp Mack, a Guy Harvey Lodge, Marina & RV Resort

3.0 star property
9.0 out of 10, Wonderful, (161)
"This was the first time I’ve ever did any type of camping in a sense. It was a wonderful experience."
The price is AU$206
includes taxes & fees
25 Nov - 26 Nov
Camp Mack, a Guy Harvey Lodge, Marina & RV Resort

Calabay Charm - sunny & private, great accommodation & space, south-facing pool/spa

9.6 out of 10, Exceptional, (18)
"Size of the home and set up was perfect for our 10 person family gathering. Management group was very responsive to the issues we identified. Two issues were noticed in the last 24 hours of our stay, so the management group had to opportunity to correct. Trash bins had trash bags from prior guests still in them, so no room for our trash bags. The outdoor grill was filthy, even though guests are asked to clean up after use, due to condition we were unable to use it. "
Calabay Charm - sunny & private, great accommodation & space, south-facing pool/spa

Lake Ida Beach Resort

3.0 star property
7.6 out of 10, Good, (159)
"Was a wonderful peaceful stay"
The price is AU$136
includes taxes & fees
2 Dec - 3 Dec
Lake Ida Beach Resort

Modern Haines City Home w/ Pool & Lanai!

8.6 out of 10, Excellent, (24)
"Had to evacuate mobile home due to hurricane- this VRBO rental home made us feel safe and it was very clean"
Modern Haines City Home w/ Pool & Lanai!

Villa Bonita. Southern Dunes 4 golf courses. Disney area!

9.6 out of 10, Exceptional, (145)
"We thoroughly enjoyed our family stay on our trip to Legoland and Orlando attractions. The property was very clean and met our needs perfectly. The pool was the icing on the cake for when kids got back or had some down time. The owner communication was top notch and very friendly and professional. Would stay here again!"
Villa Bonita. Southern Dunes 4 golf courses. Disney area!

Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney

10.0 out of 10, Exceptional, (32)
"Awesome hosts great experience all the way around "
Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney

Lovely bright high ceilings condo

9.4 out of 10, Exceptional, (51)
"Overall out stay was assume. Had a hiccup our first night, but Angela diligently worked the kinks out. And because of us not staying out first night gave us another night. And VRBO refunded out money for our hotel stay."
Lovely bright high ceilings condo

Beautiful home with white sand beach on stunning Crooked Lake

10.0 out of 10, Exceptional, (59)
"This place is just the best! The house is set up so nice and comfortable. The beach area is fun and relaxing. It was a return visit for us and we loved it just as much as the first time! We will be back!!! "
Beautiful home with white sand beach on stunning Crooked Lake

Stay and Save! Stay now through December 20th and enjoy 20% off your stay 5 nights or more!

8.4 out of 10, Very good, (33)
"Great ply"
Stay and Save! Stay now through December 20th and enjoy 20% off your stay 5 nights or more!

The ultimate Florida vacation in a tranquil, natural setting

9.0 out of 10, Wonderful, (64)
"My son and I were scheduled to stay in Tampa right after Hurricane Milton. The property was damaged so we had to make a quick change. This place was the perfect fit for what we needed! Host was very accommodating and easy to work with! Easy access to the property. Accommodations were great. Three nice size bedrooms. Property is right by the pool. It is a drive to restaurants and big box stores but we were there to fish and relax. Plenty of lakes near this property."
The ultimate Florida vacation in a tranquil, natural setting

Family-Friendly Winter Haven Home w/ Pool!

9.6 out of 10, Exceptional, (8)
"Property was clean. Was perfect for what we needed on a short notice. Definitely recommend staying. "
Family-Friendly Winter Haven Home w/ Pool!

LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES

9.2 out of 10, Wonderful, (63)
"no running water upon check in. Had to find someone to help with main water valve. Maintenance said it was not his job it was the owners (we could not get a hold of) still haven’t gotten any word from host. My husband had to find and dig up the main water line to turn it on! Thank god we checked in 30min prior, if it had been after hours I don’t know what we’d have done. I’m 6 months pregnant and we were traveling with a 3 year old. No contact with host at all during the 2 night stay. I ended up...
The price is AU$418
includes taxes & fees
30 Nov - 1 Dec
LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES

Glamping in beautiful Bartow central FL

6.0 out of 10, (1)
"It was a camper, fenced inyard, nice little yard, fire pit, chairs, nice decor and nice lights around outside. Fridge and freezer very good. Bed was not comfortable for me. Store and grill there but not easily accessible and it said to bring pots to use. No towels, i missed that part i guess. Due to delays arrived at 3 am plus last night did not stay as not comfortable. 3 day booking should have been 2."
The price is AU$146
includes taxes & fees
26 Nov - 27 Nov
Glamping in beautiful Bartow central FL

Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater

8.8 out of 10, Excellent, (71)
"Just an okay stay."
The price is AU$686
includes taxes & fees
16 Dec - 17 Dec
Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater

The Lake Alfred Citrus Wood Guest Cabin

10.0 out of 10, Exceptional, (8)
"Very cozy, clean, host was very friendly."
The price is AU$232
includes taxes & fees
27 Nov - 28 Nov
The Lake Alfred Citrus Wood Guest Cabin

Vacation Home in Haines City, Fl

9.4 out of 10, Exceptional, (8)
"There was aunt in the kitchen bad The pool was dirty seemed like the pump wasn’t working properly "
Vacation Home in Haines City, Fl

Cheerful New Construction Home

8.8 out of 10, Excellent, (27)
"11 minutes from Legoland! Super nice beautiful area. The beds were firm and hard I felt Like I was sleeping on the floor but I know every ones bed type is different I like softer bouncy like a cushion. But other than that everything was wonderful! "
The price is AU$688
includes taxes & fees
25 Nov - 26 Nov
Cheerful New Construction Home

3 Bed Villa at Southern Dunes golf course

4.4 out of 10, (14)
"The property was not clean and prepared for our arrival which I had to pay extra for to check-in in the am. blown bulbs dead batteries in more than one remote. TV not hooked up. Trash was full. house looked dirty. Pool area riddled with spider webs cigarette butts. Paid for the pool warming, it didn't happen until the afternoon before my morning departure. Worst of all my skin is shedding from the mites in the master bedroom"
3 Bed Villa at Southern Dunes golf course

Comfy house private bedroom share bathroom

10.0 out of 10, Exceptional, (5)
"it was nice."
The price is AU$154
includes taxes & fees
3 Dec - 4 Dec
Comfy house private bedroom share bathroom

Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown

9.8 out of 10, Exceptional, (30)
"10 out of 10 highly recommend. Very cute private space. Will book again."
The price is AU$194
includes taxes & fees
25 Nov - 26 Nov
Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown
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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Other types of properties in Highland Park you may be interested in

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (598)
"Great hotel. "
The price is AU$213
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Winter Haven Inn & Suites 

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
7.0 out of 10, Good, (1006)
"Property was ok, Should have been more staff at the counter, had to pay a $50 room essential fee, which we got back after the room was checked. "
The price is AU$176
includes taxes & fees
27 Nov - 28 Nov
Howard Johnson by Wyndham Winter Haven FL

Holiday Inn Winter Haven, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (1015)
"Very nice place clean "
The price is AU$170
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Winter Haven, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Highland Park?

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

What are some of the best holiday rentals that Highland Park has to offer?

Modern Haines City Home w/ Pool & Lanai!: This holiday home rental outside of Highland Park is equipped with 1 hot tub, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms and a kitchen with kitchenware.

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 wider area, you’ll find KICCO Wildlife Management Area and Lake Wailes.

What’s a holiday rental in Highland Park like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland Park. Holiday rentals feature amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family getaway.