A beach at sunset with birds flying and a person walking.

Belleair Vacations from $482

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The Latest Belleair Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Aug 28 - Aug 31

    Hibiscus Suites - Gateway to Siesta Key + Flight

    Sarasota
    3 nights
    2.5 star property
    8.6/10 - Excellent (2,378 reviews)
    "The room was clean and very nice. There was more than enough space for our family that came to visit us. The pool was nice and clean, and the shuttle service they offered was an incredible option if you don't want to drive and park at the beach."
    Reviewed July 24, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - SRQNonstop SRQ - BOSNonstop
    $690
    $482
    per traveler
    found 1 day ago
    Hibiscus Suites - Gateway to Siesta Key
  • Sep 25 - Sep 28

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    3 nights
    3.0 star property
    9.2/10 - Wonderful (562 reviews)
    "The staff was excellent! Our accommodations were very nice, very clean and well maintained. Everything we needed was right at our fingertips during our entire stay."
    Reviewed July 23, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPA1 stop TPA - BOS1 stop
    Save 100% on your flight
    $1,048
    $644
    per traveler
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Sep 25 - Sep 29

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    4 nights
    4.0 star property
    9.6/10 - Exceptional (1,107 reviews)
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPANonstop TPA - BOS1 stop
    Save 100% on your flight
    $1,182
    $762
    per traveler
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • Sep 1 - Sep 6

    ChartHouse Clearwater Beach Marina Hotel + Flight

    Clearwater Beach
    5 nights
    2.0 star property
    9.6/10 - Exceptional (1,289 reviews)
    "everything was good"
    Reviewed July 25, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPANonstop TPA - BOS1 stop
    Save 100% on your flight
    $1,099
    $743
    per traveler
    found 1 day ago
    ChartHouse Clearwater Beach Marina Hotel
  • Oct 13 - Oct 17

    voco Sarasota by IHG + Flight

    Central Sarasota
    4 nights
    3.5 star property
    9.0/10 - Wonderful (1,001 reviews)
    Roundtrip New York (JFK) - Tampa (TPA)
    JFK - TPANonstop TPA - JFKNonstop
    $753
    $527
    per traveler
    found 1 day ago
    voco Sarasota by IHG

Belleair 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

How much does a Belleair vacation package cost?

You can pick up a vacation package to this popular destination from $482 on Expedia. However, how much your vacation to Belleair costs will depend on your hotel choice, length of stay and season.

What are the cheapest months to go to Belleair?

You can usually find lower rates and greater availability in March, October and December. Check out our cheap Belleair vacation packages and you could land some great off-season deals.

How many days is enough for Belleair?

With a well-organized itinerary, you can easily hit the top Belleair sights in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Belleair vacation for longer.

How to find the best Belleair package deals?

Use Expedia's filter tool to help you find some unbeatable Belleair package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Belleair package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.

Is it cheaper to book a Belleair vacation as a package?

An Expedia vacation package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can tailor your Belleair trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

When to book a vacation package to Belleair?

Enjoy incredible discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Belleair escape.

Does Expedia offer Book Now, Pay Later Belleair vacation packages?

If you're like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Belleair trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.