A parking lot with two cars, a building with a red-tiled roof, and palm trees.

Madeira Beach Vacations from $445

Book a Hotel + Flight or Car together to unlock savings

The Latest Madeira Beach Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 24 - Sep 28

    ChartHouse Clearwater Beach Marina Hotel + Flight

    Clearwater Beach
    4 nights
    2.0 star property
    9.6/10 - Exceptional (1,278 reviews)
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - MCONonstop MCO - BOSNonstop
    Save 100% on your flight
    $815
    $445
    per traveler
    found 1 day ago
    ChartHouse Clearwater Beach Marina Hotel
  • Aug 22 - Aug 25

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    3 nights
    3.0 star property
    9.2/10 - Wonderful (561 reviews)
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - SRQ1 stop SRQ - BOS1 stop
    Save 100% on your flight
    $1,197
    $734
    per traveler
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Sep 24 - Sep 28

    CW Hotel + Flight

    Clearwater Beach
    4 nights
    4.0 star property
    9.8/10 - Exceptional (20 reviews)
    "I thoroughly enjoyed my stay at CW Clearwater. It's newly renovated so if you're looking it up right now, you may end up viewing the old, previous property. We had Suite #601 - 2 bedrooms, 2 full baths, full kitchen, and small living room with dining table and balcony facing the street (ocean view across the street). I could've spent an entire week at this location. It felt like a cozy condo. The staff is wonderful. Drinks/food waa also great."
    Reviewed July 22, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPANonstop TPA - BOS1 stop
    Save 100% on your flight
    $1,082
    $698
    per traveler
    found 1 day ago
    CW Hotel
  • Sep 12 - Sep 18

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    6 nights
    4.0 star property
    9.6/10 - Exceptional (1,100 reviews)
    "Great trip. The condo was very clean and the staff was friendly."
    Reviewed July 22, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPANonstop TPA - BOS1 stop
    Save 100% on your flight
    $1,401
    $918
    per traveler
    found 2 days ago
    Ocean Club Treasure Island Hotel
  • Sep 30 - Oct 6

    BeachTrail Lodging + Flight

    Indian Rocks Beach
    6 nights
    3.0 star property
    9.8/10 - Exceptional (101 reviews)
    "The cottage was well stocked with a snack basket and a super dog basket. The kitchen was stocked with all needed essentials and the parking also worked out well."
    Reviewed April 14, 2026
    Roundtrip New York (NYC) - Tampa (TPA)
    LGA - TPANonstop TPA - LGANonstop
    Save 100% on your flight
    $999
    $658
    per traveler
    found 1 day ago
    BeachTrail Lodging

Where to stay in Madeira Beach

Find the best Madeira Beach areas and neighborhoods for the activities you enjoy most. Learn more about Madeira Beach
Learn more about Madeira Beach

Bay Pines

Close to the water, this St. Petersburg community is surrounded by attractions, from the beach to waterways and dining districts.

Discover the most popular places to visit in Madeira Beach

What to do in Madeira Beach

Madeira 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

How much does a Madeira Beach vacation package cost?

You can snap up a vacation package to this popular destination from $445 on Expedia. But how much your vacation to Madeira Beach costs will depend on the season, length of stay and hotel choice.

What are the cheapest months to go to Madeira Beach?

If you're hoping to score a cheap Madeira Beach vacation package, consider visiting in June, September and October. You'll generally find lower rates on flights and accommodations during these months — ideal for travelers wishing to save money.

How many days is enough for Madeira Beach?

With around 3 days, you'll have plenty of time to visit popular neighborhoods like South Pinellas Community Council and La Vista during your Madeira Beach vacation. Be sure to also add Hubbards Marina and John's Pass Village & Boardwalk to your list of must-sees. In the mood for more adventures? Consider exploring outside of Madeira Beach on day trips and tours.

Is it worth booking a vacation package to Madeira Beach?

Popular for its coastal beaches, festivals and fishing, a Madeira Beach vacation is a hit with all kinds of visitors. Be sure to visit main sights like John's Pass Village & Boardwalk and Hubbards Marina, and consider renting some wheels for day trips to experience even more.

How to find the best Madeira Beach package deals?

Bagging a cheap Madeira Beach package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Madeira Beach package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.

Is it cheaper to book a Madeira Beach vacation as a package?

An Expedia vacation package could score you significant savings when compared to booking accommodations and flights separately. Better still, you can customize your Madeira Beach getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.

When to book a vacation package to Madeira Beach?

Secure incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Madeira Beach adventure.

How to plan a trip to Madeira Beach?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Madeira Beach.
  2. Set a budget: Factor in expenses like flights, food and transportation when working out how much to save for your trip to Madeira Beach. Then, select a hotel that suits your budget, whether that's a wallet-friendly stay or a swankier retreat.
  3. Use Expedia's trip planning tool to discover Madeira Beach: Research every aspect of your trip to Madeira Beach with this handy planner. Invite your friends and family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Work out your trip length: Consider how much time you'd like to spend discovering Madeira Beach. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Madeira Beach vacation package that brings all your bookings together.
  6. Book any excursions or activities: Here's the fun part — locking in everything you want to see and do. Explore some of the top things to do in Madeira Beach and reserve your tickets in advance to save time (and maybe some cash too!).

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

If you're like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Madeira Beach trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.

Book with confidence

Things to do in and around Madeira Beach

Madeira Beach is perfect for family vacations and offers a variety of activities. Visitors can enjoy shopping at local centers and exploring the boardwalk. Key attractions include boat tours, ocean excursions, exciting adventures at Adventure Island, fishing trips, and numerous water activities. Whether you're looking to relax on the beach or seek adventure, Madeira Beach has something for everyone.

Shopping

Experience shopping at John's Pass Village & Boardwalk in Madeira Beach, featuring entertainment and a vibrant atmosphere. For a unique find, visit the Flea Market Wagon Wheel just 4 miles away, or check out Largo Mall, located 7 miles away, offering a mix of family-friendly shopping and fun.

Recreation

At War Veteran Memorial Park, enjoy peaceful surroundings perfect for relaxation and mindfulness. Bardmoor Golf and Tennis Club offers a vibrant outdoor experience with golf and tennis, while Smugglers Cove Adventure Golf provides family-friendly fun with its adventurous mini-golf course, ideal for all ages.

Adventure

At Splash Harbour Water Park, located 7 miles from Madeira Beach, enjoy thrilling water slides and a lazy river, perfect for family fun. Treasure Island Fun Center, 3 miles away, offers exciting arcade games for all ages. Explore the scenic Pinellas Trail, 6 miles distant, ideal for hiking and outdoor adventures.

Nightlife

Experience the vibrant nightlife at Madeira Beach with live music at The Frog Pond. For a laid-back vibe, enjoy cocktails at the friendly Caddy's on the Beach. If you're in the mood for dancing, check out the lively atmosphere at the nearby John's Pass Village and Boardwalk.

Find the best attractions near Madeira Beach

Madeira Beach, Florida, is an ideal destination for family beach vacations, offering a blend of sandy beaches and cultural experiences. Visitors can explore popular attractions such as local art museums and modern universities, while enjoying the beautiful coastal scenery. With its famous beach getaways and access to some of the best beaches in the area, including nearby Siesta Beach, Madeira Beach caters to those seeking relaxation and outdoor adventures alike.

  • Upham Beach: Located 5 miles from Madeira Beach, Upham Beach offers a serene retreat with soft sands and gentle waves. Perfect for sunbathing, swimming, or beachcombing, it captures the quintessential Florida beach vibe.
  • Salvador Dali Museum: A short 10-mile drive takes you to the Salvador Dali Museum, where you can explore the eccentric works of the surrealist artist. The museum's unique architecture and vibrant exhibits provide a rich cultural experience.
  • Eckerd College: Situated 9 miles away, Eckerd College boasts beautiful waterfront views and a modern campus. Stroll through its gardens and enjoy the city vibes that blend academia with nature.

Best time to go to Madeira Beach

The best time to visit Madeira Beach is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Tips to save on your trip to Madeira Beach

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically September to November) for more affordable package holidays to Madeira Beach.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.