Winter Beach Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Winter Beach Vacation

When a getaway to the city is calling, answer it with a Winter Beach vacation package. The neighborhood of Seagrove, which is good for cafes, coastal beaches and nature, makes an awesome base for your adventures. Fill your free time with visits to Holman Stadium, Pelican Island National Wildlife Refuge and Wabasso Beach Park, some of the things you just have to see during a trip to Winter Beach. That dream Winter Beach vacation is a couple of clicks away. Search flights, accommodations and more on Expedia for an adventure that's tailored to suit your style.

Top Winter Beach Vacation Deals

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

Seasons Florida Resort

2 out of 5
Price was CA $1,913, price is now CA $963 per person
CA $963
per person
Jan 1 - Jan 8
found 11 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9/10 Wonderful! (4,064 reviews)
It was a clean and quaint little spot. It had all the things I needed for a restful stay.

Reviewed on Oct 26, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was CA $4,439, price is now CA $2,259 per person
CA $2,259
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (565 reviews)

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was CA $3,420, price is now CA $1,881 per person
CA $1,881
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was CA $2,194, price is now CA $1,250 per person
CA $1,250
per person
Jan 1 - Jan 8
found 11 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.6/10 Exceptional! (1,234 reviews)

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was CA $1,626, price is now CA $1,029 per person
CA $1,029
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.4/10 Very good! (7,259 reviews)

Ready to book your vacation to Winter Beach?

 

Choose your dates

Winter Beach Hotel Deals

Hutchinson Island Hotel

Hutchinson Island Hotel

2.5 out of 5
1230 Seaway Drive Fort Pierce FL
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Nov 18 to Nov 19
CA $147
CA $191 total
Nov 18 - Nov 19
includes taxes & fees
Hutchinson Island Hotel
Capt Hiram's Resort

Capt Hiram's Resort

3 out of 5
1580 US Highway 1 Sebastian FL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Nov 1 to Nov 2
CA $139
CA $184 total
Nov 1 - Nov 2
includes taxes & fees
Capt Hiram's Resort
Ocean Breeze Inn Vero Beach

Ocean Breeze Inn Vero Beach

3.5 out of 5
3384 Ocean Dr Vero Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Oct 28 to Oct 29
CA $214
CA $240 total
Oct 28 - Oct 29
includes taxes & fees
8.8/10 Excellent! (1,259 reviews)
"We were there for only one night, only complaint was the room smelled musty due to being on the water!"

Reviewed on Oct 25, 2026

Ocean Breeze Inn Vero Beach
See all 1,705 properties in Winter Beach
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Winter Beach

Clear Kayak Tours in Fort Pierce

Clear Kayak Tours in Fort Pierce

CA $127
per adult
Clear Kayak Tours in Fort Pierce
Sebastian Inlet Half-Day Sandbar Charter

Sebastian Inlet Half-Day Sandbar Charter

CA $990
per traveller
Sebastian Inlet Half-Day Sandbar Charter
See all activities in Winter Beach

Frequently asked questions

How much does a Winter Beach vacation package cost?
You'll find cheap prices from CA $963 on Expedia for your Winter Beach getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winter Beach costs.
What are the cheapest months to go to Winter Beach?
If you'd like to book a cheap Winter Beach vacation package, consider travelling in January, February and August. You're likely to find lower rates on hotels and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Winter Beach?
To fully enjoy a Winter Beach vacation, we recommend staying for 3 days. Split your time between discovering Vero Beach Municipal Marina, Vero Beach Museum of Art and other well-known attractions, in addition to exploring neighbourhoods like Central Beach and Gifford. If you've got some time to spare, add a tour or day trip to your Winter Beach vacation itinerary.
How to find the best Winter Beach package deals?
Use Expedia's filters to help you find some of the best Winter Beach package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Winter Beach package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Winter Beach vacation as a package?
You can enjoy significant savings on your next Winter Beach retreat by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter Beach?
If you're considering an impromptu Winter Beach adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Winter Beach?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Winter Beach.
  2. Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will likely be the largest expense during your trip to Winter Beach.
  3. Decide how long to go for: Now that you're more familiar with Winter Beach, you can figure out the right length of your vacation. Put together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your accommodations and airfare: Once you've nailed down your travel dates and duration, book the right Winter Beach vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.