Deals on vacations and trips to Highland Park

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Highland Park flight + hotel vacation packages

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
Save 100% on your flight
Price was $850, price is now $467 per person
$467
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,316, price is now $748 per person
$748
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,759, price is now $1,088 per person
$1,088
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.
The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was $1,453, price is now $925 per person
$925
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,217, price is now $785 per person
$785
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Tampa (TPA)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

Top Highland Park hotels deals

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Free Cancellation
$99 nightly
The price is $111 total per night
$111 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
$282 nightly
The price is $316 total per night
$316 total
Aug 12 - Aug 13
Total with taxes and fees
This smoke-free hotel features a water park, 2 outdoor pools, and a restaurant. Unwind with a drink at the bar/lounge and enjoy perks like free full breakfast and free WiFi. Valet parking, express check-in, and luggage storage are also offered.
Pool
Breakfast included
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
5801 Roosevelt Dr Winter Haven FL
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $134 total per night
$134 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features an outdoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
$170 nightly
The price is $191 total per night
$191 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with a drink at the poolside bar and enjoy the free full breakfast each morning. Self parking and a safe deposit box are also offered on site.
Pool
Breakfast included
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $95 total per night
$95 total
Jul 19 - Jul 20
Total with taxes and fees
This motel features a restaurant, an outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pool
Breakfast included
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW Winter Haven FL
Free Cancellation
$100 nightly
The price is $112 total per night
$112 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features an outdoor pool and a gym. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A lobby fireplace, a computer station, and luggage storage are also on offer.
Pool
Breakfast included
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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.

Frequently asked questions

How much are vacation packages to Highland Park?
Exciting adventures await in Highland Park, with Travelocity vacation packages from as low as $467. Providing both hotels and flights, these awesome deals make it a breeze to experience all corners of the world.
Where can I get the best vacation package deals for Highland Park?
You'll discover a terrific range of Highland Park package deals on Travelocity. With 400 partner airlines and 1,000,000 worldwide properties, putting together the perfect escape will be simple.
Why should I purchase my Highland Park vacation package via Travelocity?
Because we believe in crafting one-of-a-kind vacation experiences. From flights and hotels to car rentals and activities, our packages make traveling a breeze. Our customer support team is available 24/7 to ensure you'll never wander alone. We also have an amazing Price Match Guarantee, so you can book your vacation knowing you've landed the best deal around.
Can I save money on my Highland Park car rental if I book it with a hotel or flight?
Certainly — bundle your car, hotel and flight into a Highland Park vacation package and you can save a tidy sum. With so much to see and do in the Highland Park area, that set of wheels will make exploring a breeze. Once you've settled into the driver's seat, turn up the stereo and head to Universal Studios Florida, a must-see sight around 45 mi from Highland Park.
Which airport is best for Highland Park?
Highland Park has a couple of major airports to choose from — Orlando Intl. Airport (MCO) (40 mi away from the city center) and Tampa Intl. Airport (TPA) (60 mi away from central Highland Park).

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