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.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,637, price is now $876 per person
$876
per person
Dec 2 - Dec 9
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.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,777, price is now $1,129 per person
$1,129
per person
Nov 18 - Nov 23
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 picnic area are also on offer.
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $4,272, price is now $2,730 per person
$2,730
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
A private beach and an outdoor pool are featured at this hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. Enjoy the hot tub and perks like free self parking and free WiFi.
Azul Resort

Azul Resort

2 out of 5
South Village
Save 100% on your flight
Price was $1,486, price is now $963 per person
$963
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
Siesta Key Inn

Siesta Key Inn

2 out of 5
South Village
Save 100% on your flight
Price was $1,553, price is now $1,017 per person
$1,017
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden and express check-out are also provided.

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
$110 nightly
The price is $123 total per night
$123 total
Oct 25 - Oct 26
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
$253 nightly
The price is $284 total per night
$284 total
Oct 28 - Oct 29
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
$122 nightly
The price is $137 total per night
$137 total
Oct 18 - Oct 19
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
$244 nightly
The price is $273 total per night
$273 total
Oct 30 - Oct 31
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
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
$134 nightly
The price is $150 total per night
$150 total
Oct 18 - Oct 19
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
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
$144 nightly
The price is $161 total per night
$161 total
Oct 20 - Oct 21
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 $876. 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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