Highland Park Holidays from £963
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Your Highland Park Holiday
Save time and energy on your travel planning with a Highland Park holiday package. A good neighbourhood to base yourself in this vibrant city is Cypress Gardens, which is good for families and much more besides. Bok Tower Gardens, Mountain Lake and KICCO Wildlife Management Area are just some of the many sights worth checking out during your trip to Highland Park. Expedia has what you need to escape your routine. Tailor your holiday to Highland Park to suit your style of travel, whatever that may be!
Top Highland Park Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Captiva Beach Resort
South Village
£963
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LHR) to Tampa (TPA)
9/10 Wonderful! (1,303 reviews)
Stayed 09/18/2026 and as usual... it was perfect! Always clean, comfortable and affordable. Thank you for a wonderful stay.
Reviewed on 20 Sept 2026
Landing Tampa Westshore
Port Tampa City
£1,351
per person
23 Nov - 30 Nov
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
9/10 Wonderful! (197 reviews)
All was wonderful. We had a problem with the concrete curbs. The curb grabbed our bumper and pulled the front end of our bumper off when we had to back out. It has cost us several thousand dollars for the repairs. Otherwise it was a beautiful facility.
Reviewed on 21 Sept 2026
Inn on the Beach - 18+ only
Pass-a-Grille
£1,284
per person
21 Nov - 28 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Tampa (TPA)
9.8/10 Exceptional! (444 reviews)
Fantastic property! The Inn on the Beach is right on the beach. Staff is amazing. Loved the access to beach chairs and towels. Highly recommend!
Reviewed on 16 Sept 2026
Highland Park Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 230 |
Max Temp Winter | 21ºC |
Max Temp Summer | 32ºC |
Top Sights | Jump Florida Skydiving, Tiger Creek Preserve and KICCO Wildlife Management Area |
Top hotels in Highland Park
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
£92
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Room with king size bed. Comfortable and clean. Nice desk but I didn’t really have a chance to use it since I was only there overnight. Breakfast was included. It was ok. Nothing special,"
Reviewed on 20 Sept 2026
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
£196
22 Sept - 23 Sept
includes taxes & fees
LEGOLAND Beach Retreat
100 Legoland Way SE Winter Haven FL
£164
12 Oct - 13 Oct
includes taxes & fees
8.6/10 Excellent! (379 reviews)
"Look behind the bunk"
Reviewed on 21 Sept 2026
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
Central Florida Half-Day Private Birding Activity - 2 person max
£257
per traveller
Ladies Luncheon Pontoon Tour (Gentleman welcome)
£73
per adult
Frequently asked questions
Why should I book my Highland Park holiday with Expedia?
Expedia has you covered for every aspect of your upcoming Highland Park getaway. You'll always get the best prices around, but when you bundle your accommodation, airfares and/or car hire into a holiday package, you'll score even bigger savings. Want to really make the most of your break? Add some awesome tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so there's no need to worry if your travel plans change. Head over to our Customer Service Portal link to find out more.
When is the best time of year to holiday in Highland Park?
Peak season falls in January, February and March and is a thrilling time to visit — but be prepared for bigger crowds and longer queues. May, June and July are typically quieter times of the year. With average daytime temperatures of 16ºC, January is the coolest month in Highland Park. The warmest time of year is June, when you can expect average temperatures of 27ºC during the day. Whatever the weather conditions, you'll discover plenty of things to keep you occupied here.
What is the top hotel for my holiday in Highland Park?
Offering lots of amenities and a cosy place to stay, Budget Inn will make the ideal base for your Highland Park getaway.
How do I get a cheap holiday to Highland Park?
If you love amazing deals, bundle your bookings into a Highland Park holiday. Whether you're searching for hotels, flights, day tours or hire cars, you can browse and book them all in one place. You'll have ample choice at your fingertips as well. Expedia has more than 400 airlines and 321,000 hotel options around the world to choose from. Fly with who you want, stay where you like and save a tidy sum — now that's the ideal getaway! Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Highland Park holiday?
Offering must-see tourist attractions such as Bok Tower Gardens and Eagle Ridge Mall, a holiday in Highland Park is packed with exciting things to do and see. Mountain Lake and Jump Florida Skydiving are two other sights worth exploring.
Do I need a visa for my Highland Park holiday?
Official government websites have all the information you need on visa requirements, application procedures and necessary documentation. Your nationality and reason for visiting, whether it be for work or pleasure, will determine if you need a visa for Highland Park. Also check that your passport is up to date and has a minimum of six months validity remaining beyond the date of your intended return. Do all your travel planning well ahead of time to avoid any last-minute surprises.
What should I wear on my Highland Park holiday?
Do a little research into the types of things people in Highland Park wear, and maybe even look up social media fashion pages for inspiration. Whatever your look, aim to create a versatile wardrobe filled with pieces that suit your destination and show off your personal style. Daytime temperatures during January, Highland Park's coolest month, average 16ºC. June marks this destination's warmest month when average temperatures reach 27ºC. Our advice? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Highland Park holiday include?
Choose from a combination of hire cars, flights and hotels. Once you've made your booking, add some tours and activities. Want to pick your fare class? That's also easy to do. The choice is yours when it comes to planning your dream Highland Park getaway. Expedia allows you the flexibility and freedom to tailor the holiday you've always wanted, your way.
Does Expedia offer Book Now, Pay Later Highland Park holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in manageable instalments. Simply select the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your trip. Don't forget to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:
- Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna can help. Paying in convenient monthly instalments will make that dream holiday possible.
- No-deposit holidays: Hitting the "book now" button is much easier with this plan. With no upfront fee for your getaway, you can Book Now, Pay Later and start working on your travel itinerary.
Can I choose my airline with a Highland Park Expedia holiday?
You sure can. We offer more than 400 partner airlines worldwide, so choose the carrier that's a good fit for your budget needs.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
