Winter Haven Vacations
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Winter Haven Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton
Downtown Tampa
$1,010
per person
Dec 28 - Jan 3
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Book a stay at this historic hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.
Nice enough place, but the location didn't really support the pricing of this location, plus the bums asking for money etc. Outside the establishments main doors. With that comes with the three guys heckling our beautiful wives, just because we were not with them. Then the walls are thin enough you can hear the lady next door getting railed by her man. Real Classy! Thanks for nothing.
Reviewed on Oct 5, 2026
CW Resort
$1,935
per person
Dec 28 - Jan 3
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
Room was huge. Got the 2bed/2bath. Immaculate condition, cleanest hotel I’ve ever stayed in. Didn’t use the pool or hot tub. watched dolphins swim in the marina from the balcony. Great location. Definitely coming back
Reviewed on Oct 7, 2026
The Hotel Zamora
$1,329
per person
Dec 28 - Jan 3
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Fort De Soto Park and John's Pass Village & Boardwalk are located nearby.
Plaza Beach Hotel Beachfront Resort
$1,122
per person
Dec 28 - Jan 3
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.
The property and staff were amazing! We stayed in the Gulf View Balcony King room aka "the best room in the house" and it did not disappoint! We will be coming back to St. Pete and staying with Plaza Beach again soon! Clean, right on the beach, and amazing staff!
Reviewed on Oct 7, 2026
Blue Wave Suites
$1,647
per person
Dec 28 - Jan 3
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
The staff made this experience so worth it . It includes beach supplies tents chairs toy no need to worry . Will return definitely. 2 min walk from beach
Reviewed on Oct 2, 2026
The Don CeSar
$2,094
per person
Dec 28 - Jan 3
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Tampa (TPA)
Book a stay at this beach resort in St. Pete Beach. Enjoy a full-service spa, 2 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Fort De Soto Park and John's Pass Village & Boardwalk are located nearby.
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See all available trips from Columbus to Winter Haven
View all tripsWinter 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 38156 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
200 Cypress Gardens Boulevard Winter Haven FL
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr Winter Haven FL
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
305 5th St NW and Avenue D NW Winter Haven FL
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
1 Legoland Way Winter Haven FL
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
1300 3rd St Winter Haven FL
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
14501 Grove Resort Avenue Winter Garden FL
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
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
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 ...
Margaritaville Resort Orlando with H2O Waterpark
8000 Fins Up Circle Kissimmee FL
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. ...
Vacation Village Orlando, Celebration
2975 Arabian Nights Blvd Kissimmee FL
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 ...
Hilton Vacation Club Mystic Dunes Orlando
7600 Mystic Dunes Lane Kissimmee FL
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
2900 Parkway Blvd Kissimmee FL
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 ...
Holiday Inn Club Vacations at Orange Lake Resort by IHG
8505 W Irlo Bronson Memorial Hwy Kissimmee FL
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. ...
Holiday Inn Resort Kissimmee by the Parks by IHG
3011 Maingate Ln Kissimmee FL
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean ...
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
5711 W Irlo Bronson Memorial Hwy Kissimmee FL
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 ...
Omni Orlando Resort at ChampionsGate
1500 Masters Blvd Davenport FL
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 ...
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.
Mon, Nov 16 - Fri, Dec 4
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$58
Roundtrip
found 1 day ago
Tue, Nov 3 - Sat, Nov 7
BOS
Logan Intl.
TPA
Tampa Intl.
$179
Roundtrip
found 10 hours ago
Tue, Nov 3 - Tue, Nov 10
BOS
Logan Intl.
TPA
Tampa Intl.
$179
Roundtrip
found 11 hours ago
Tue, Feb 2 - Fri, Feb 19
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$185
Roundtrip
found 2 days ago
Tue, Nov 3 - Sat, Nov 7
BOS
Logan Intl.
TPA
Tampa Intl.
$194
Roundtrip
found 10 hours ago
Best neighborhoods in Winter Haven
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More Types of Hotels
- Hotels with Air Conditioning in Winter Haven
- Family Hotels in Winter Haven
- Hotels with WiFi in Winter Haven
- Hotels with a Pool in Winter Haven
- Hotel with wifi in Winter Haven
- Hotels with Complimentary Breakfast in Winter Haven
- Cheap Hotels in Winter Haven
- Lakefront Hotels in Winter Haven
- Pet-friendly Hotels in Winter Haven
- Hotels with Bars in Winter Haven
- Smoke Free Hotels in Winter Haven
- Hotels with Balconies in Winter Haven
- Resorts & Hotels with Spas in Winter Haven
- Hotels with smoking rooms in Winter Haven
- Luxury Hotels in Winter Haven
- Hotels with Hot Tubs in Winter Haven
- Beach Hotels in Winter Haven