Winter Haven Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Winter Haven Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
CW Resort

CW Resort

$652
per person
Oct 22 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) 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.
Everything was perfect

Reviewed on Sep 20, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

$1,366
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
A place to relax and enjoy the beach.

Reviewed on Sep 20, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
$847
per person
Oct 21 - Oct 25
found 6 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Won’t Be Staying Here Again! Very disappointing experience. We were told over the phone around 1 PM that our room was available for early check-in and that we could go to the hotel. The man I spoke with was not particularly helpful and initially told me that the only way to find out was to come to the hotel. I specifically explained that I didn’t want to drive there just to find out that we had to wait and asked if he could simply check whether a room was available. He then told me that our room was available and that we could come. We left the beach specifically to go to the hotel (4 adults, a kid, and a dog), only to arrive around 2:15 PM and be told the room wasn’t ready yet but would be soon. No one followed up with us, and we ended up waiting for almost **2 hours** until I had to go back to the front desk at 4 PM (our official check-in time) to ask about the room. Also, we had an extra car and were told parking was completely full, forcing us to park elsewhere and pay a significant amount. However, we noticed many empty spaces throughout the night (up to 1 am), which made it feel like the front desk simply didn’t want to help. On top of that, the $80/day pet fee seemed very unreasonable. The property itself was nice, but the poor communication, parking situation, and extra fees made the stay frustrating. **We would not stay here again.**

Reviewed on Sep 20, 2026

The Avalon Club

The Avalon Club

Save 100% on your flight
$935
per person
Oct 22 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Tampa (TPA)
Stay at this aparthotel in Clearwater Beach. Enjoy a fitness center, parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
lo que más me gusta es que esta muy cerca de la playa

Reviewed on Sep 20, 2026

Crystal Palms Beach Resort

Crystal Palms Beach Resort

Sunshine Beach
$715
per person
Oct 22 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) 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.
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

Downtown Tampa
Save 100% on your flight
$990
per person
Oct 22 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.
Great location, secure self parking, helpful staff. Rooms were clean and functional, but don’t expect fancy, high-end touches. Great value for your money though, I’d return for sure. We didn’t try on location restaurant as there are plenty of options nearby.

Reviewed on Sep 21, 2026

Don't see what you're looking for?
See all available trips from Columbus to Winter Haven
View all trips

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 38356 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 breakfast (surcharge). Our guests praise the breakfast and the ...
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 ...
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 ...
Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

3151 Sunset Walk Drive Kissimmee FL
37.36 km from city center
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and room service. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood ...
Don't see what you're looking for?
See all available properties in Winter Haven
View all properties
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
Sun Country Airlines