Highland Park Holidays

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Top Flight + Hotel Deals in Highland Park

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was €1,090, price is now €862 per person
€862
per person
4 Aug - 9 Aug
found 1 day ago
Return flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,179 reviews)
Very clean and bright, wife loved it.

Reviewed on 4 Jul 2026

CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was €1,509, price is now €1,018 per person
€1,018
per person
4 Aug - 9 Aug
found 1 day ago
Return flight included
Toronto (YTO) to Tampa (TPA)
No reviews

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was €2,030, price is now €1,439 per person
€1,439
per person
4 Aug - 9 Aug
found 1 day ago
Return flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (561 reviews)
10/10 would recommend this property. Clean, freindly staff, complimentary coffee bar, and great location are just some of the perks of staying here. The rooftop bar and pool is a nice way the wind down your day that included a comp glass of champagne amd views of awesome sunsets. The property also offered access to free beach chairs and umbrellas for use on the beach which is a huge plus in my book. Numerous stores and restaurants well within walking distance of the hotel. So if your looking for a nice hotel while visiting CWB, look no further. You will not be disappointed. We will definitely be returning on our next beach vacation.

Reviewed on 1 Jul 2026

The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was €1,787, price is now €1,275 per person
€1,275
per person
4 Aug - 9 Aug
found 1 day ago
Return flight included
Toronto (YTO) to Tampa (TPA)
6/10 (3 reviews)

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was €1,383, price is now €995 per person
€995
per person
4 Aug - 9 Aug
found 1 day ago
Return flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (3,408 reviews)
Helpful, clean, attentive - very close to the beach 10/10

Reviewed on 4 Jul 2026

Top hotels in Highland Park

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
The price is €108 per night from 26 Jul to 27 Jul
€108
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"It was a nice stay . Breakfast should be complementary"

Reviewed on 4 Jul 2026

Holiday Inn Winter Haven by IHG
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is €339 per night from 6 Jul to 7 Jul
€339
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (151 reviews)
"The hotel rooms were fantastic! All that my kid was hoping for. The pool was small."

Reviewed on 3 Jul 2026

Legoland Florida Hotel
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
2953 Ridge Way Lake Wales FL
Fully refundable
The price is €128 per night from 12 Jul to 13 Jul
€128
12 Jul - 13 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Rooms..linens..bathrooms were all clean..conveniently located to shopping and dining and attractions..but the carpeting in the lobby and rooms needs cleaning has an odor. Staff was very professional and helpful..great breakfast."

Reviewed on 29 Jun 2026

Holiday Inn Express Lake Wales N-Winter Haven by IHG
See all 1,488 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.

What to do in Highland Park

LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

€75
per traveller
LEGOLAND Florida FasTrack Pass
Horse Petting

Central Florida Adventure Park - Authentic Dude Ranch Experience

€21
per adult
Central Florida Adventure Park - Authentic Dude Ranch Experience
Winter Haven: Coffee, Tea & Dessert Food Tour

Winter Haven: Coffee, Tea & Dessert Food Tour

€115
per adult
Winter Haven: Coffee, Tea & Dessert Food Tour
See all activities in Highland Park

Frequently asked questions

How much does a Highland Park holiday package cost?
You can pick up a holiday package to this top destination from €862 on Expedia. However, how much your holiday to Highland Park costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Highland Park?
January, February and July are great times to search for cheap Highland Park holiday packages. Choosing to travel in less busy months means you can generally find lower prices on hotels and flights.
How many days is enough for Highland Park?
With a well-organised schedule, you can easily tick off the most popular Highland Park attractions in a handful of days. But if you prefer to discover hidden spots or go on day tours, consider booking your Highland Park holiday for longer.
How to find the best Highland Park package deals?
Start your search for a Highland Park package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Highland Park package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Highland Park getaway off to a flying start.
Is it cheaper to book a Highland Park holiday as a package?
You can enjoy significant savings on your next Highland Park break by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Highland Park?
If you're considering an impromptu Highland Park trip, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Highland Park?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Highland Park.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to save for your trip to Highland Park. Then, pick a property that works with your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Decide how long to go for: Now that you're up to speed on Highland Park, you can work out the perfect length of your holiday. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Highland Park holiday package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.