Deals on vacations and trips to Winter Haven

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Winter Haven flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $531, price is now $289 per person
$289
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Tampa (TPA)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A garden, a library, and a picnic area are also on offer.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $663, price is now $393 per person
$393
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip non-stop 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 $979, price is now $584 per person
$584
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip non-stop 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 $869, price is now $537 per person
$537
per person
Aug 27 - Aug 30
found 18 hours ago
Roundtrip 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 Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,038, price is now $687 per person
$687
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.

Top Winter Haven 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
$110 nightly
The price is $123 total per night
$123 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
$295 nightly
The price is $330 total per night
$330 total
Aug 2 - Aug 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
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 9 - Jul 10
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
$111 nightly
The price is $124 total per night
$124 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
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
$238 nightly
The price is $268 total per night
$268 total
Aug 4 - Aug 5
Total with taxes and fees
Free water park access, 3 restaurants, and 6 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Enjoy the 2 hot tubs and perks like free WiFi.
Pool
Hot Tub
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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.

Stay near popular Winter Haven attractions

A detailed model of a cityscape with various buildings, including a tall skyscraper, a modern building, and a historic building with a red roof.

LEGOLAND® Florida

9.0/10 (2,150 reviews)
Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.
See properties

Frequently asked questions

How much are vacation packages to Winter Haven?
Travelocity provides package deals to Winter Haven, including flights and hotels, starting from an impressive $289. With all the extra money, you could book some cool tours or even add a couple of extra days to your getaway.
How long should my Winter Haven vacation be?
Many travelers pack their suitcase and vacation in Winter Haven for about 2 nights. That's a great guide, but don't feel limited by it. Whether you only stay for a couple of days to see the famous attractions or settle in to uncover hidden gems, an unforgettable journey awaits.
Where can I get the best vacation package deals for Winter Haven?
Travelocity will be able to help you find an awesome Winter Haven package deal. With as many as 400 partner airlines and 1,000,000 properties across the world, there's no doubt you'll find the perfect mix.
Why should I book my Winter Haven vacation package with Travelocity?
With our Price Match Guarantee, we'll match any lower price you find. Add to that our 24/7 customer support and top-shelf service and your dream vacation is well within reach.
Will I save money on my Winter Haven car rental if I bundle it with a hotel or flight?
Certainly — bundle your hotel, flight and car into a Winter Haven vacation package and you can save loads. With so much to see and do in the Winter Haven area, that rental vehicle will make exploring a joy. Once you've buckled up, get out on the wide open road and cruise toward Universal Studios Florida, a well-known sight roughly 35 mi from Winter Haven.
Which airport is best for Winter Haven?
Many people choose to fly into Orlando Intl. Airport (MCO), 40 mi northeast of downtown Winter Haven. Others prefer Tampa Intl. Airport (TPA) (50 mi away from central Winter Haven) or Orlando Sanford Intl. Airport (SFB) (60 mi away from central Winter Haven).
What is there to do in Winter Haven?
You'll notice a certain kind of magic as you stroll through the streets of Winter Haven. LEGOLAND® Florida and Chain of Lakes Park are just two famous sights that make this city so special, so put them on your itinerary.
Where should I stay when visiting Winter Haven?
Many people hit the hay at the Holiday Inn Winter Haven, an IHG Hotel. It's sure to be a good base for your Winter Haven vacation.

Photos of local treasures

Browse Winter Haven vacation photos for more inspiration

A castle entrance with flags and banners, including a LEGO Kingdoms banner.
A tree with hanging moss and sunlight filtering through the leaves.
A detailed LEGO model of a cityscape with prominent buildings like Luxor and a pyramid structure.
A pathway surrounded by large trees with extensive root systems.
A LEGO figure with a red face and a staff.

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