Winter Haven Vacations from $307

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Winter Haven vacation packages

Price found within the past 48 hours. Click for updated prices.
Rio Hotel & Casino, a Destination by Hyatt Hotel

Rio Hotel & Casino, a Destination by Hyatt Hotel

4 out of 5
Save 100% on your flight
Price was $704, price is now $307 per person
$307
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Las Vegas (LAS)
15.6/10 Exceptional! (6,658 reviews)
I will definitely stay here again. The room was clean and really nice. It was also pretty big. The staff is awesome! My new fave place to stay in Vegas

Reviewed on Nov 14, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $2,424, price is now $920 per person
$920
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
16/10 Exceptional! (1,004 reviews)
Room was clean and spacious. Property did not have available microwave for guest. House keeping was good but did not replace soap or drinking glass. Gym not located in main hotel area and it closes at 5pm. Overall property is beautiful and good amenities.

Reviewed on Nov 7, 2025

Broadmore Miami Beach

Broadmore Miami Beach

3.5 out of 5
North Beach
Price was $1,556, price is now $592 per person
$592
per person
Jan 22 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
5.6/10 (369 reviews)
Staff was very nice

Reviewed on Nov 4, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $1,277, price is now $531 per person
$531
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
18.4/10 Exceptional! (2,007 reviews)
The staff was very friendly. We were able to leave our luggage before check in and after checkout. Complimentary beverages and refills were provided. I booked through third party and no issues with reservation. We had the family suite which included 2 full beds, 1 king, 2 bathrooms. It was very clean and perfect size for 4 adults.

Reviewed on Nov 14, 2025

Creekside Inn

Creekside Inn

2.5 out of 5
Price was $770, price is now $339 per person
$339
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1,009 reviews)
The staff was very courteous. Room was older but clean and bed was comfortable. ~ tile floors needed to be cleaned with another product- they felt slimy. Shower head needed to be replaced

Reviewed on Nov 11, 2025

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

Discover the most popular places to visit in Winter Haven

Jefferson Park

Explore the great outdoors at Jefferson Park, a lovely green space in Carrizo Springs. Take in the art scene while you're in the area.

Jefferson Park

Winter Haven Hotel Deals

EL Dorado ranch resort

EL Dorado ranch resort

2.5 out of 5
5150 Farm to Market 191, Crystal City, TX
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $125 total per night from Nov 24 to Nov 25
$125 total
Nov 24 - Nov 25
Total with taxes and fees
8.4/10 Very Good! (33 reviews)
Great Job

Reviewed on Nov 14, 2025

EL Dorado ranch resort
Hampton Inn Carrizo Springs

Hampton Inn Carrizo Springs

2.5 out of 5
2651 North US Highway 83, Carrizo Springs, TX
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $196 total per night from Dec 7 to Dec 8
$196 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (152 reviews)
Very quiet and relaxing. Room was comfortable and clean.

Reviewed on Nov 8, 2025

Hampton Inn Carrizo Springs
Super 8 by Wyndham Carrizo Springs

Super 8 by Wyndham Carrizo Springs

2 out of 5
137 La Lomita Drive, Carrizo Springs, TX
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $202 total per night from Nov 16 to Nov 17
$202 total
Nov 16 - Nov 17
Total with taxes and fees
7.8/10 Good! (114 reviews)
Could have used stairs in more places.

Reviewed on Nov 8, 2025

Super 8 by Wyndham Carrizo Springs
See all 24 properties in Winter Haven
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.

Find the Best Winter Haven Vacation Packages

Winter Haven Essential Information

Language
English
Currency
U.S dollars
Top Sights
Jefferson Park and Carrizo Springs Golf Course

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winter Haven vacation package cost?
You'll find cheap prices from $307 on Expedia for your Winter Haven getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
If you're hoping to book a cheap Winter Haven vacation package, consider traveling in February, November and December. You're likely to find better prices on hotels and flights during these months — perfect for a budget-friendly break.
How many days is enough for Winter Haven?
Typically, a handful of days is enough to explore the major sights during your Winter Haven vacation. But if you prefer to have some time to kick back or take day tours, consider extending your itinerary.
How to find the best Winter Haven package deals?
Landing a cheap Winter Haven package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Winter Haven package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Winter Haven vacation as a package?
You can enjoy significant savings on your Winter Haven escape by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter Haven?
If you've got your Winter Haven vacation dates finalized, book as soon as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Winter Haven vacation packages?
Your Winter Haven break is meant to be an escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.