Winter Haven Vacations from $378

Book a Hotel + Flight or Car together to unlock savings

The Latest Winter Haven vacation packages

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $894, price is now $378 per person
$378
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (NYC)
18.4/10 Exceptional! (2,007 reviews)
Great room and polite staff and excellent restaurant and location.

Reviewed on Nov 15, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $2,228, price is now $895 per person
$895
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
19.2/10 Exceptional! (53 reviews)
Lovely property. Staff service inconsistent overall. Room was not serviced one day. On the day there was construction above pool area, no notice was sent out. Pool area staff/manager and construction crew didn't seem to be on the same page.

Reviewed on Nov 13, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $11,702, price is now $5,187 per person
$5,187
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
16/10 Exceptional! (1 review)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,598, price is now $713 per person
$713
per person
Jan 16 - Jan 19
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
16/10 Exceptional! (1,004 reviews)
Enjoyed a few days with the kids gere

Reviewed on Nov 15, 2025

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

4.5 out of 5
Hollywood
Price was $1,290, price is now $583 per person
$583
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)
18.4/10 Exceptional! (79 reviews)
This apartment was perfect for what we needed. It is central to many parts so you could walk if you wanted. We did rent a car so it was great that free parking for 2 spots was available. It was clean and had everything we needed for our short stay. I'd likely come and stay again when I am back in the area

Reviewed on Nov 10, 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 17 to Nov 18
$202 total
Nov 17 - Nov 18
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 $378 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.