A marina with boats docked, a large building on the left, and a city skyline in the background.

Winter Beach Vacations from $330

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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.

The Latest Winter Beach Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 12 - Jan 16

    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort + Flight

    Kissimmee
    4 nights
    2.0 star property
    9.0/10 - Wonderful (4,098 reviews)
    "Todo esta muy bien, limpio, servicial los empleados"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $644
    $330
    per traveler
    found 1 day ago
    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
  • Jan 12 - Jan 16

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,235
    $615
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Jan 10 - Jan 16

    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight

    International Drive District
    6 nights
    3.0 star property
    7.8/10 - Good (636 reviews)
    "It was a newly remodeled property. Everything was real nice. Ran smooth. Would definitely stay there again."
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $848
    $441
    per traveler
    found 1 day ago
    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
  • Jan 28 - Feb 1

    Ocean Landings Resort and Racquet + Flight

    Cocoa Beach
    4 nights
    2.5 star property
    7.2/10 - Good (52 reviews)
    "This is an older property but very clean and well maintained. The two ocean front buildings are under a major renovation but there is still access to the beach. We would stay again."
    Reviewed October 30, 2026
    Roundtrip • Philadelphia (PHL) - Orlando (MCO)
    TTN - MCO • Nonstop SFB - TTN • Nonstop
    Save 100% on your flight
    $761
    $431
    per traveler
    found 1 day ago
    Ocean Landings Resort and Racquet
  • Jan 12 - Jan 16

    Meliá Orlando Celebration + Flight

    Celebration
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,643 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $686
    $403
    per traveler
    found 1 day ago
    Meliá Orlando Celebration

Winter Beach Hotel Deals

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.

Frequently Asked Questions

Is Winter Beach better suited for a beach vacation or a cultural trip?

Winter Beach is primarily a beach and outdoor destination, ideal for travelers seeking sun, sand, and natural beauty. The area is known for its inviting coastline, with popular spots like Indian River Shores Beach and Sebastian Inlet State Park Beach offering opportunities for swimming, sunbathing, and water activities. Nature enthusiasts will also appreciate Sebastian Inlet State Park, which provides scenic views and outdoor adventures.


The destination also has a local history, once known as "Quay" before being renamed for promotional purposes as "Where the Sunshine Spends the Winter." A Winter Beach vacation package is best suited for those prioritizing relaxation and outdoor experiences.

How can I save money on a Winter Beach vacation package?

When you bundle, you can save up to 30%*. To save money on a Winter Beach package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What are the top things to do in Winter Beach?

For a Winter Beach vacation, you'll find plenty of outdoor activities and natural attractions to explore:


Browse and book things to do in Winter Beach on Expedia to enhance your best vacation packages in Winter Beach.

Do you need to rent a car in Winter Beach, or is public transport enough?

For a Winter Beach vacation package, renting a car is generally recommended to fully explore this outdoor and nature destination. While many resorts provide on-site amenities and dining, a car offers the flexibility to visit attractions like Sebastian Inlet State Park, about 4 miles from central Winter Beach, or Indian River Shores Beach, about 6 miles away.


Winter Beach is accessible via several airports, including Orlando International Airport (MCO) and Orlando Melbourne International Airport (MLB), and a rental car simplifies travel from these locations. For those booking Winter Beach vacation packages with flights, having a car helps provide convenient access to the area's diverse beaches and natural sights. Local taxis and ride-share apps are also available for shorter journeys.

Can I change or cancel my Winter Beach vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Winter Beach vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Winter Beach vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winter Beach vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Winter Beach?

To find last-minute vacation packages to Winter Beach, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Winter Beach vacation packages?

Free cancellation on a Winter Beach vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Winter Beach vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Winter Beach getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Winter Beach vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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