Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Highland Park vacation rentals

A modern reception area with a wooden panel design, a tiled floor, and a white door in the background.

1. Elita Inn

Elita Inn
3.0 star property
Dundee
7.2 out of 10, Good, (39 reviews)
"Great p"
United States
Gilles
$85 nightly
The price is $95
Nov 11 - Nov 12
Total with taxes and fees
Elita Inn
A lakeside dock with boats, a wooden structure with a metal roof, and dense trees in the background.

2. Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (226 reviews)
"Camp Mack is an awesome place for getting away for a few days or longer. The surroundings are beautiful, and the people are so friendly."
United States
Terri
$110 nightly
The price is $123
Nov 15 - Nov 16
Total with taxes and fees
Camp Mack Lodge, Marina & RV Resort
A modern hotel room with a bed, a sofa, a TV, and a fireplace.

3. Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake

Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
Lake Wales
8.0 out of 10, Very good, (4 reviews)
"Room was spotless. Private entrance, the shuffleboard table game was fun, coffee and creamer was awesome. Bedding was so soft. You could tell there was construction going on with in the property however there wasn’t any noice and the room was clean clean clean!!! "
United States
Barbara
$154 nightly
The price is $171
Nov 30 - Dec 1
Total with taxes and fees
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
A bedroom with a stone fireplace, a large bed, and a view of the outdoors through large windows.

4. Lake View•Gardens•Private Balcony Suite•Legoland

Lake View•Gardens•Private Balcony Suite•Legoland
Lake Wales
9.2 out of 10, Wonderful, (13 reviews)
"Great view, comfortable room for our one night stay."
United States
Vern H.
$135 nightly
The price is $150
Nov 11 - Nov 12
Total with taxes and fees
Lake View•Gardens•Private Balcony Suite•Legoland
Two lounge chairs with metal frames and grey fabric seats, positioned near a pool with a tiled edge.

5. Lake Front! Spacious Home w/heated pool & kayaks

Lake Front! Spacious Home w/heated pool & kayaks
Lake Wales
10.0 out of 10, Exceptional, (28 reviews)
"It’s a lovely, quiet location "
United States
Kathy M.
$416 nightly
The price is $462
Nov 11 - Nov 12
Total with taxes and fees
Lake Front! Spacious Home w/heated pool & kayaks
A swimming pool with lounge chairs and palm trees, surrounded by a modern building with large windows and string lights.

6. Lake Retreat w/Pool & Hot Tub near Bok Tower

Lake Retreat w/Pool & Hot Tub near Bok Tower
Lake Wales
9.8 out of 10, Exceptional, (78 reviews)
"Great place to stay. Lots of room and a great view. I will definitely try to book it again next time I am In town!!"
United States
Jeremy G.
$503 nightly
The price is $559
Nov 11 - Nov 12
Total with taxes and fees
Lake Retreat w/Pool & Hot Tub near Bok Tower
A spacious indoor area with a seating area, a counter, and a kitchen visible in the background.

7. Dundee | 2 Queen Bed Nmsk

Dundee | 2 Queen Bed Nmsk
Dundee FL
10.0 out of 10, Exceptional, (90 reviews)
"Location is close to Legoland, so perfect for families visiting with kids."
United States
Anonymous traveler
$90 nightly
The price is $99
Nov 11 - Nov 12
Total with taxes and fees
Dundee | 2 Queen Bed Nmsk
A balcony with a grill, a dining area, and a kitchen visible through an open door.

8. Cozy Retreat Near Crooked Lake with Gym, Games & Deck Views

Cozy Retreat Near Crooked Lake with Gym, Games & Deck Views
Babson Park
8.8 out of 10, Excellent, (15 reviews)
"cozy , quiet , nice relaxing stay "
United States
Kevin K.
$303 nightly
The price is $338
Nov 21 - Nov 22
Total with taxes and fees
Cozy Retreat Near Crooked Lake with Gym, Games & Deck Views
An indoor swimming pool with a clear view of the sky through a metal roof structure.

9. Hotel Style Lakeview Cottage • 3BR • Heated Pool

Hotel Style Lakeview Cottage • 3BR • Heated Pool
Lake Wales
$242 nightly
The price is $269
Nov 11 - Nov 12
Total with taxes and fees
Hotel Style Lakeview Cottage • 3BR • Heated Pool
A modern kitchen with white cabinetry, granite countertops, stainless steel appliances, and a wooden floor.

10. Modern Dundee Townhome Near Lakes & Legoland!

Modern Dundee Townhome Near Lakes & Legoland!
3.5 star property
Dundee
$316 nightly
The price is $353
Nov 12 - Nov 13
Total with taxes and fees
Modern Dundee Townhome Near Lakes & Legoland!
An outdoor hot tub area with a pool, surrounded by chairs and a table.

11. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
9.8 out of 10, Exceptional, (78 reviews)
"Great location"
United States
Michelle
$288 nightly
The price is $319
Nov 15 - Nov 16
Total with taxes and fees
Legoland Splash Escape with pool and hot tub!
A modern kitchen with built-in appliances, a dining area with a table and chairs, and a hallway leading to a door.

12. Premium Lake Wales Getaway!

Premium Lake Wales Getaway!
Lake Wales
9.8 out of 10, Exceptional, (6 reviews)
"Jill & Kayla, thank you do mich for the wonderful stay. I look forward visiting again"
United States
Dawn H.
$276 nightly
The price is $307
Nov 11 - Nov 12
Total with taxes and fees
Premium Lake Wales Getaway!
A modern kitchen with a central island, pendant lighting, and a view of the outdoors.

13. Lakefront Pool Retreat • Theater 7.1 • Fishing

Lakefront Pool Retreat • Theater 7.1 • Fishing
Lake Wales
$339 nightly
The price is $377
Nov 11 - Nov 12
Total with taxes and fees
Lakefront Pool Retreat • Theater 7.1 • Fishing
A swimming pool with a fence, lounge chairs, and a palm tree.

14. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (198 reviews)
"Clean room and private area loved it"
United States
Heather
$68 nightly
The price is $76
Nov 27 - Nov 28
Total with taxes and fees
Lake Ida Beach Resort
A bedroom with a bed, a TV, a sofa, and a wardrobe.

15. Poolside Suite | 98” TV | Sleeps 7 | 3 Rooms

Poolside Suite | 98” TV | Sleeps 7 | 3 Rooms
Lake Wales
$194 nightly
The price is $215
Nov 11 - Nov 12
Total with taxes and fees
Poolside Suite | 98” TV | Sleeps 7 | 3 Rooms
A modern living room with a dining area, a flat-screen TV mounted on the wall, and a ceiling fan.

16. Cozy 3 bedroom house in a beautiful Winter Haven area near Legoland and Boktower

Cozy 3 bedroom house in a beautiful Winter Haven area near Legoland and Boktower
Winter Haven
10.0 out of 10, Exceptional, (4 reviews)
"The home was lovely for our weekend visit! Alecia has everything that you need, and her back porch is great to hang out and drink coffee. We really enjoyed our stay."
United States
victoriah p.
$300 nightly
The price is $333
Nov 11 - Nov 12
Total with taxes and fees
Cozy 3 bedroom house in a beautiful Winter Haven area near Legoland and Boktower
A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

17. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
$127 nightly
The price is $141
Nov 22 - Nov 23
Total with taxes and fees
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
Private kitchen

18. Peaceful Place

Peaceful Place
Winter Haven
10.0 out of 10, Exceptional, (28 reviews)
"Great property!"
United States
Glenn C.
$364 nightly
The price is $404
Nov 11 - Nov 12
Total with taxes and fees
Peaceful Place
A wooden deck leading to a dock over water, surrounded by grass and trees with Spanish moss.

19. Stilt House on the Shore at Lake Reedy

Stilt House on the Shore at Lake Reedy
Frostproof
10.0 out of 10, Exceptional, (4 reviews)
"Great place to stay. It was perfect for our family. Great spot on the lake. Very quiet and peaceful. Will definitely return in the future. "
United States
Thomas C.
$245 nightly
The price is $272
Nov 17 - Nov 18
Total with taxes and fees
Stilt House on the Shore at Lake Reedy
A modern kitchen with white cabinetry, granite countertops, stainless steel appliances, and a wooden floor.

20. Modern Dundee Townhome Near Lakes & Legoland!

Modern Dundee Townhome Near Lakes & Legoland!
Dundee
10.0 out of 10, Exceptional, (1 review)
"The Host Zinna was amazing! If we had any questions they were answered in a timely fashion! The rental was beautiful! I would for sure stay here again with my family!"
United States
Becca F.
$306 nightly
The price is $340
Nov 12 - Nov 13
Total with taxes and fees
Modern Dundee Townhome Near Lakes & Legoland!
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

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven

10/10 Excellent

The hotel room was beautiful and was very clean. I had an excellent stay and would come back.
United States
Ricardo
Reviewed January 18, 2024
Best Western Plus Winter Haven Inn & Suites 

Find out more about Highland Park

Everything you need to know about Highland Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland Park vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $76 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland Park rentals

At Expedia, we put the best Highland Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Disney Family Retreat, 3 Bedroom with Private Pool/Spa and Game Room: 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. Make the most of the hot tub in this rental home to help you unwind.

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 Twin Lakes.

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.

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