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.
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and laundry facilities.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.
Barsala At The Wayland Condos

Barsala At The Wayland Condos

4 out of 5
per person
Sep 6 - Sep 12
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
This aparthotel features an outdoor pool and a gym. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Hampton Inn & Suites Clearwater Beach

Hampton Inn & Suites Clearwater Beach

3.5 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
A private beach and an outdoor pool are featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. Enjoy a meal from the restaurant and perks like free buffet breakfast and free WiFi.

Top Winter Haven hotels deals

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
Get rates
An outdoor pool is featured at this hotel, along with free WiFi in public areas and a fireplace in the lobby. Enjoy the free continental breakfast each morning. A computer station, luggage storage, and laundry facilities are also on offer.
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
Get rates
An outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like full breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.
Pool
Breakfast included
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
Get rates
2 hot tubs, an outdoor pool, and a 24-hour gym are all featured at this smoke-free resort. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Get rates
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. Relax with a drink at one of the 3 poolside bars and enjoy the 2 hot tubs and 24-hour gym.
Pool
Hot Tub
Vacation Village at Parkway

Vacation Village at Parkway

3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
Get rates
7 outdoor pools, 7 hot tubs, and a gym are all featured at this smoke-free condo. Bring the family and enjoy the children's pool, playground, and arcade/game room. WiFi in public areas is free.
Pool
Hot Tub
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
Get rates
This smoke-free resort features free water park access, a full-service spa, and 3 restaurants. Bring the family and enjoy the lazy river, waterslide, and arcade/game room. Enjoy the 3 outdoor pools 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.

Popular places to visit

Legoland Florida which includes a pond, a river or creek and rides

LEGOLAND® Florida

4.5/5(1,082 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.

LEGOLAND® Florida

Chain of Lakes Park

4/5(84 reviews)

Catch an event at Chain of Lakes Park during your trip to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Chain of Lakes Park

Winter Haven Hospital

Though Winter Haven Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Winter Haven while you are here.

Winter Haven Hospital

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 $473. 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

Winter Haven showing rides
Winter Haven
Legoland Florida featuring rides and signage
Winter Haven which includes a park
Legoland Florida showing rides, outdoor art and a statue or sculpture