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.
Resort Sixty-Six

Resort Sixty-Six

2.5 out of 5
Save 100% on your flight
Price was $1,201, price is now $812 per person
$812
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
A restaurant and an outdoor pool are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $2,373, price is now $1,148 per person
$1,148
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,515, price is now $824 per person
$824
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,341, price is now $842 per person
$842
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
A marina, a 24-hour gym, and a restaurant are all featured at this Mediterranean hotel. Unwind with a drink at one of the 3 bars/lounges and enjoy freebies like WiFi in public areas and a beach shuttle. You'll appreciate the outdoor pool, poolside bar, and concierge services.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,228, price is now $825 per person
$825
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

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
$100 nightly
The price is $112 total per night
$112 total
Sep 10 - Sep 11
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
$247 nightly
The price is $277 total per night
$277 total
Sep 2 - Sep 3
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
$114 nightly
The price is $128 total per night
$128 total
Sep 3 - Sep 4
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
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
$121 nightly
The price is $136 total per night
$136 total
Sep 6 - Sep 7
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
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
$234 nightly
The price is $262 total per night
$262 total
Sep 11 - Sep 12
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
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
Free Cancellation
$123 nightly
The price is $138 total per night
$138 total
Sep 6 - Sep 7
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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 $812. 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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