Winter Haven Vacations

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Winter Haven Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn By Marriott Tampa Downtown

Residence Inn By Marriott Tampa Downtown

Downtown Tampa
$582
per person
Nov 12 - Nov 16
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.
This is my second time staying at this location. I like the convenience of being close to everything downtown. There was construction this time around so a little more hectic and loud. I do not love the parking situation and that I have to go across the street, use a parking garage and if it is a busy time you may not find a spot since you can only park in designated areas. Would like to see the breakfast be a little more upgraded. Overall I give it a good rating because it is a good hotel choice.

Reviewed on Aug 26, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
$1,018
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.
Clean, friendly & helpful staff. Wish the refrigerator had an ice maker and the coffee maker was a Nesspresso and you couldn’t buy the pods in a store. They need one that uses pods like a kuerig.

Reviewed on Aug 26, 2026

CW Resort

CW Resort

Save 100% on your flight
$627
per person
Nov 12 - Nov 16
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

Save 100% on your flight
$828
per person
Nov 12 - Nov 16
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
The bed was so bad I could barely walk after sleeping in it. I literally had to sleep on the floor or chase lounger. Horrible

Reviewed on Aug 27, 2026

Captiva Beach Resort

Captiva Beach Resort

South Village
Save 100% on your flight
$614
per person
Nov 12 - Nov 16
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Crystal Palms Beach Resort

Crystal Palms Beach Resort

Sunshine Beach
Save 100% on your flight
$611
per person
Nov 12 - Nov 16
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy a 24-hour front desk, dry cleaning or laundry services, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
We have been visiting this property for over 15 years and had a few worries when reading the feedback regarding the refurbishment. We have recently stayed for a 3 week holiday and can honestly say it has been the best experience we have had, from check in to check out everything was very smooth and we had no problems what so ever. The cleanliness of our unit was much better than we have seen in recent years. It seems that the new management have really put time and effort into the property. Thank you for a wonderful stay and we will be back soon.

Reviewed on Aug 22, 2026

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Winter Haven Vacation Packages

Trying to figure out a way to package your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Winter Haven perfect. In only a few clicks, you can select the best vacation package for you. AARP Travel Center has an amazing list of flights and hotels, as well as local activities to select from.

Winter Haven Hotels

You can choose from around 38607 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Winter Haven hot spots, we have plenty of options available.

From Winter Haven hotels with pools and on-site restaurants, to boutique accommodations that add all the thoughtful touches, you'll get a hotel here that will make your trip amazing. With AARP Travel Center's Winter Haven hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.

Things to do in Winter Haven

Winter Haven has around 37,689 people that make this city their home. If you needed a break from the hustle of a big city, then you are in the right spot. Guests come to enjoy Winter Haven's options for leisure activities and a landscape that draws travelers from all over the country.

If you're making this a family getaway, then you are in luck. Winter Haven has a theme park close by. You can spend an afternoon at Legoland Florida riding rides, testing your skills, and amusing the kid in everyone.

The AARP Travel Center "Things to Do" page has more great activities that you can book.

Save with a Winter Haven Vacation Package

As an AARP Member, you can benefit from all the great savings. You can save on select hotels worldwide, flights, and car rentals. No matter what vacation package you pick, you can rest easy knowing that you already saved on your trip. So what are you waiting for? Book today and get ready for your Winter Haven vacation.

Top Hotel Deals

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL
2.23 km from city center
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful ...
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

5801 Roosevelt Dr Winter Haven FL
5.52 km from city center
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

305 5th St NW and Avenue D NW Winter Haven FL
0.39 km from city center
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
Legoland Florida Hotel

Legoland Florida Hotel

1 Legoland Way Winter Haven FL
5.21 km from city center
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida ...
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

1300 3rd St Winter Haven FL
1.48 km from city center
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL
38.57 km from city center
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL
37.53 km from city center
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ...
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

2975 Arabian Nights Blvd Kissimmee FL
40.05 km from city center
Book a stay at this family-friendly aparthotel in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean ...
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL
37.52 km from city center
Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL
38.35 km from city center
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL
35.53 km from city center
Book a stay at this golf hotel in Kissimmee. Enjoy free WiFi, 4 outdoor pools, and a golf course. Our guests praise the pool and the restaurant in our reviews. ...
Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

2900 Parkway Blvd Kissimmee FL
39.96 km from city center
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, 2 outdoor pools, and 4 restaurants. Our guests praise the pool and the helpful staff ...
Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

1500 Masters Blvd Davenport FL
28.6 km from city center
Book a stay at this spa hotel in Four Corners. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

5711 W Irlo Bronson Memorial Hwy Kissimmee FL
40.83 km from city center
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Galleria Palms Hotel

Galleria Palms Hotel

3000 Maingate Ln Kissimmee FL
37.56 km from city center
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
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See all available properties in Winter Haven
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
JetBlue Airways
Delta
American Airlines
United
Wed, Sep 30 - Tue, Oct 6
EWR
Newark Liberty Intl. Airport
TPA
Tampa Intl.
$189
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Sep 30 from Newark Liberty Intl. Airport to Tampa Intl., returning Tue, Oct 6, priced at $189 found 4 hours ago