Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Outdoor pool, pool umbrellas, pool loungers
Lake Ida Beach Resort
3.0 star property
7.4 out of 10, Good, (157)
"Was a wonderful peaceful stay"
The price is NZ$136
includes taxes & fees
31 May - 1 Jun
Lake Ida Beach Resort
Cabin, 1 Bedroom (Cabin 61) | Living area
Camp Mack, a Guy Harvey Lodge, Marina & RV Resort
3.0 star property
9.2 out of 10, Wonderful, (156)
"The best bang for your buck! "
The price is NZ$222
includes taxes & fees
2 Jun - 3 Jun
Camp Mack, a Guy Harvey Lodge, Marina & RV Resort
Property grounds
Calabay Charm - sunny & private, great accommodation & space, south-facing pool/spa
9.8 out of 10, Exceptional, (10)
"This home accommodated our group of 6 adults very comfortably. Well laid out, lots of room to gather together or find some quiet time. Pool area offers both sun and shade and is very private. We would return."
Calabay Charm - sunny & private, great accommodation & space, south-facing pool/spa
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Outdoor dining
Modern Haines City Home w/ Pool & Lanai!
9.0 out of 10, Wonderful, (19)
"Clean and everything well. AC worked well. Would love to have a grill to cook poolside."
Modern Haines City Home w/ Pool & Lanai!
Property grounds
Villa Bonita. Southern Dunes 4 golf courses. Disney area!
9.6 out of 10, Exceptional, (131)
"It was great"
Villa Bonita. Southern Dunes 4 golf courses. Disney area!
Outdoor pool, a heated pool
☀️🌴Award-Winning Golf, Disney/Universal, Pool, Clubhouse/Gated Community 🌴☀️
10.0 out of 10, Exceptional, (62)
"We had a very nice month at this property. Great communication with the owner. We left something behind and she is going to mail it to us therefore, I believe going above and beyond."
☀️🌴Award-Winning Golf, Disney/Universal, Pool, Clubhouse/Gated Community 🌴☀️
Outdoor pool, a heated pool
Lovely bright high ceilings condo
9.6 out of 10, Exceptional, (48)
"Was a nice place to stay."
Lovely bright high ceilings condo
Pool
Tropical Disney Villa: Internet, pool, golf-view, games room &...a treasure hunt
9.0 out of 10, Wonderful, (74)
"Great place. Clean. Pool is great. Treasure hunt was a awesome bonus. Beds leave something to he desired. When we got there the toilet paper was half used with no replacments but over all super satisfied"
Tropical Disney Villa: Internet, pool, golf-view, games room &...a treasure hunt
A heated pool
Disney dreams, special 28ft pool with water streamers & mood lights
10.0 out of 10, Exceptional, (118)
"The house more than met our needs. With two primary suites it was just what we needed since we were traveling with my mother that is 93. The house was very clean except the glasses in the cabinet which we had to wash. The pool was perfect for our granddaughter to have a good time. We did quite a bit of cooking and everything we needed was available. We would definitely stay here again."
Disney dreams, special 28ft pool with water streamers & mood lights
Sun-loungers, beach towels
Beautiful home with white sand beach on stunning Crooked Lake
10.0 out of 10, Exceptional, (49)
"Great time. Awesome host👍👍"
Beautiful home with white sand beach on stunning Crooked Lake
Fridge, microwave, oven, stovetop
Luxury 5 BR 4.5 BA Villa - Large Pool Area and Spa, Not Overlooked, Games Room
9.6 out of 10, Exceptional, (95)
"The house was perfect! It was big enough, the pool was AMAZING, the heating was well worth the extra cost for us! Minimal issues, but when an issue did arise, the property management company was super friendly and helpful! Would absolutely recommend this property!"
Luxury 5 BR 4.5 BA Villa - Large Pool Area and Spa, Not Overlooked, Games Room
Terrace/patio
Cheerful New Construction Home
9.0 out of 10, Wonderful, (19)
"Must have been a newer rental as the amenities were scarce - however when we questioned the owner he next day delivered the kitchen utensils we asked about so very responsive. The door code was also incorrect upon check in but owner quickly set a new code within 10 minutes remotely. Everything else was good."
The price is NZ$712
includes taxes & fees
30 May - 31 May
Cheerful New Construction Home
Exterior
Luxury 4 BR /3 BA Villa - Pool/Spa Not Overlooked, Games Room
9.8 out of 10, Exceptional, (151)
"Beautiful home, they have everything you might need and more. Comfy beds, plenty of linens. Great pool. We really enjoyed staying ,in this home. You won't regret booking this home."
Luxury 4 BR /3 BA Villa - Pool/Spa Not Overlooked, Games Room
Fridge, microwave, oven, stovetop
Luxury StayComfy at WinterHeaven
7.8 out of 10, Good, (10)
"The house is newly remodeled and they did a great job. Furniture and beds are comfortable. Kitchen is well equipped but did lack dishwasher tabs, towels and detergent. The first night we were there, a large street party started across the road around 9 PM and continued until 2:30 AM. There were vehicles with loud music blaring riding past. It may have been a one-off special event as those attending were dressed up. Not at all the fault of the host. He said we could call police but I hesitated...
Luxury StayComfy at WinterHeaven
Exterior
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 NZ$523
includes taxes & fees
30 May - 31 May
LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES
Property grounds
Glamping in beautiful Bartow central FL
The price is NZ$151
includes taxes & fees
1 Jun - 2 Jun
Glamping in beautiful Bartow central FL
1 bedroom, in-room safe, desk, iron/ironing board
Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown
9.6 out of 10, Exceptional, (25)
"Alway clean, Everything to need and more. Small and Quaint. "
The price is NZ$184
includes taxes & fees
6 Jun - 7 Jun
Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown
TV, books
Winter Haven Vacation Rental w/ Private Pool!
10.0 out of 10, Exceptional, (3)
"very clean comfotable house in quite neighborhood. neighbors did not seem to care that house was VRBO house. house was just as advertised and a lot of extra amenities from the host we appreciated ( cookies , Keurig coffee pods…) we stayed for weekend while in town for tournament. great house for. a very good orice."
Winter Haven Vacation Rental w/ Private Pool!
Exterior
Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney
10.0 out of 10, Exceptional, (26)
"I rented this cottage for my mother and I to celebrate Mothers Day. We went to Bok Tower gardens and had a great time!"
Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney
Balcony
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
Don't see what you're looking for?
See all available properties in Highland Park
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.

Other types of properties in Highland Park you may be interested in

Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room)
Best Western Plus Winter Haven Inn & Suites 
2.5 star property
9.4 out of 10, Exceptional, (348)
"My son is handicapped and the room was large are clean!"
The price is NZ$231
includes taxes & fees
6 Jun - 7 Jun
Best Western Plus Winter Haven Inn & Suites 
Blackout curtains, iron/ironing board, free cots/infant beds
Howard Johnson by Wyndham Winter Haven FL
2.0 star property
7.0 out of 10, Good, (1002)
"Breakfast has a pancake maker "
The price is NZ$170
includes taxes & fees
6 Jun - 7 Jun
Howard Johnson by Wyndham Winter Haven FL
Bar (on property)
Holiday Inn Winter Haven, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (957)
"The staff were really attentive and plesant. My husband really liked that they were very easy to access and ask for coffee. The water pressure was a little weak and there were cracks in door where it looks like someone had pounded on it in the bathroom. When I told front desk they offered to move us. It was really just cosmetic so we stayed put."
The price is NZ$201
includes taxes & fees
9 Jun - 10 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Highland Park holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Highland Park. 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 Highland Park. Seeing all the best attractions is bound to make you fall in love with Highland Park. Who knows, you may even be tempted to extend your 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 holiday 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 Highland Park short-term rentals, that won’t be hard to do.

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?

Calabay Charm - sunny & private, great accommodation & space, south-facing pool/spa: This holiday home rental outside of Highland Park offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Grand Hotel and Crooked Lake.

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.

Recent reviews of Highland Park properties
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