Winter Haven Vacations from $370

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The Latest Winter Haven vacation packages

Price found within the past 48 hours. Click for updated prices.
Las Vegas Hilton at Resorts World

Las Vegas Hilton at Resorts World

4.5 out of 5
Las Vegas Strip
Save 100% on your flight
Price was $749, price is now $370 per person
$370
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8.8/10 Excellent! (14,911 reviews)
Nice hotel

Reviewed on Oct 26, 2026

Avi Lux Stay

Avi Lux Stay

4.5 out of 5
East Fort Lauderdale
Price was $1,256, price is now $548 per person
$548
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

4 out of 5
Spring Valley
Save 100% on your flight
Price was $793, price is now $378 per person
$378
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Las Vegas (LAS)
8.8/10 Excellent! (1,013 reviews)

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 $30,111, price is now $14,857 per person
$14,857
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Broadway Suites Downtown by RocketStay

Broadway Suites Downtown by RocketStay

3.5 out of 5
Coral Way
Price was $1,840, price is now $908 per person
$908
per person
Dec 31 - Jan 7
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8.6/10 Excellent! (230 reviews)
Muy bien ubicado, limpio, buena relación precio calidad

Reviewed on Aug 9, 2026

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Winter Haven Hotel Deals

Western Inn & Suites

Western Inn & Suites

2.5 out of 5
2611 US-83 Carrizo Springs TX
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Nov 27 to Nov 28
$134 total
Nov 27 - Nov 28
Total with taxes and fees
Western Inn & Suites
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
$92 nightly
The price is $104 total per night from Oct 29 to Oct 30
$104 total
Oct 29 - Oct 30
Total with taxes and fees
EL Dorado ranch resort
Wintergarden Inn

Wintergarden Inn

2.5 out of 5
2516 N Highway 83 Crystal City TX
Fully refundable
$62 nightly
The price is $70 total per night from Oct 28 to Oct 29
$70 total
Oct 28 - Oct 29
Total with taxes and fees
Wintergarden Inn
See all 27 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

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Frequently asked questions

How much does a Winter Haven vacation package cost?
You'll find cheap prices from $370 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.