A beach with people, a lifeguard tower, and tall buildings in the background.

Clearwater Beach Vacations from $414

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The Latest Clearwater Beach Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 27 - Oct 31

    BlockHaven near Legoland & Disney + Flight

    Winter Haven
    4 nights
    3.5 star property
    10/10 - Exceptional (6 reviews)
    "esta muy bien la casa acondicionada y organizada y limpia y tiene todas las comodidades para la estadía"
    Reviewed June 27, 2026
    Roundtrip New York (NYC) - Tampa (TPA)
    EWR - TPA1 stop TPA - EWR1 stop
    Save 100% on your flight
    $585
    $414
    per traveler
    found 9 hours ago
    BlockHaven near Legoland & Disney
  • Sep 14 - Sep 19

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    5 nights
    3.0 star property
    9.2/10 - Wonderful (568 reviews)
    "Will stay there again. Very convenient location near everything one might need while on vacation. Cottage was very clean and well equipped. Staff was very friendly and helpful."
    Reviewed August 3, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - SRQ1 stop SRQ - BOS1 stop
    Save 100% on your flight
    $1,863
    $1,071
    per traveler
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Oct 10 - Oct 16

    St Pete Beach Suites + Flight

    St. Pete Beach
    6 nights
    3.0 star property
    9.2/10 - Wonderful (1,003 reviews)
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPANonstop TPA - BOSNonstop
    Save 100% on your flight
    $1,464
    $920
    per traveler
    found 10 hours ago
    St Pete Beach Suites
  • Oct 8 - Oct 14

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    6 nights
    4.0 star property
    9.6/10 - Exceptional (1,136 reviews)
    "This really is a nice and clean property, very well-maintained, they have so many staff members around and it’s obvious they really care about the place! Great view of the beach and sunset from our very private balcony on the 6th floor! The room was well-stocked with everything we needed. I highly recommend this place and would come back!"
    Reviewed August 4, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPANonstop TPA - BOS1 stop
    Save 100% on your flight
    $1,616
    $1,091
    per traveler
    found 12 hours ago
    Ocean Club Treasure Island Hotel
  • Oct 11 - Oct 15

    Hibiscus Suites - Gateway to Siesta Key + Flight

    Sarasota
    4 nights
    2.5 star property
    8.6/10 - Excellent (2,393 reviews)
    "We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
    Reviewed August 3, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPA1 stop TPA - BOS1 stop
    $771
    $546
    per traveler
    found 1 day ago
    Hibiscus Suites - Gateway to Siesta Key

Where to stay in Clearwater Beach

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

Island Estate

Island Estate delivers a luxurious waterfront experience just minutes from Clearwater Beach. This exclusive residential enclave offers upscale vacation homes with private pools and boat docks along crystal-clear waters. Palm-lined streets lead to Mediterranean-style mansions where privacy and tranquility reign supreme. Gentle waves lap against private seawalls while Gulf breezes rustle through manicured landscapes. Though dining options are limited within the neighborhood, the vibrant attractions of Clearwater Beach and Pier 60 await just a short drive away.

Sand Key

Sand Key combines pristine beaches with upscale comfort along Florida's beautiful Gulf Coast. This barrier island offers a peaceful alternative to bustling Clearwater Beach just minutes away. Luxury resorts and condos line the waterfront, giving guests spectacular sunset views over the turquoise waters. Sand Key Park anchors the area with its white sand shores and nature trails through coastal hammocks. Water lovers can swim in the clear Gulf or try paddleboarding along the calm shoreline. Resort pools and beachfront lounges provide perfect relaxation spots after exploring the park's natural beauty.

Clearwater Point

Clearwater Point peninsula wraps around pristine Gulf waters with sugar-white sand beaches and stunning sunset views. This upscale retreat features modern high-rise condominiums and luxury resorts just steps from the shoreline. Waterfront promenades offer scenic strolls along three sides of this tranquil getaway. Visitors can enjoy sophisticated dining with fresh seafood while watching the sun sink below the horizon. Water activities abound from swimming to parasailing. Despite its refined atmosphere, Clearwater Point maintains easy access to nearby attractions like Sand Key Park.

Carlouel

Carlouel offers an exclusive retreat within Clearwater Beach where luxury meets Gulf Coast tranquility. Private waterfront homes line the pristine beaches, providing direct access to the crystal-clear waters of the Gulf of Mexico. The quiet, tree-lined streets create a peaceful haven away from busier tourist areas. This upscale residential enclave focuses on privacy rather than commercial attractions. Visitors appreciate the uncrowded beaches and stunning sunset views across the azure waters. While dining and shopping require a short trip to nearby areas, the serene atmosphere and high-end amenities make Carlouel perfect for travelers seeking an elegant beach escape.

Diamond Isle

Diamond Isle sits on the pristine shores of Clearwater Beach, offering an exclusive waterfront escape. Sugar-sand beaches and emerald Gulf waters create a luxurious backdrop for high-end vacation homes. Private walkways along the Intracoastal Waterway provide peaceful spots to enjoy spectacular water views. This upscale residential enclave focuses on privacy and tranquility rather than bustling tourist attractions. Visitors appreciate the quiet atmosphere and proximity to nearby Pier 60 and Clearwater Beach Municipal Marina. The neighborhood's modern luxury architecture blends seamlessly with tropical landscaping and coastal charm.

Discover the most popular places to visit in Clearwater Beach

What to do in Clearwater Beach

Clearwater 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 Clearwater Beach vacation package cost?

You can snap up a vacation package to this top destination from $414 on Expedia. However, how much your vacation to Clearwater Beach costs will depend on the season, length of stay and hotel choice.

What are the cheapest months to go to Clearwater Beach?

August, September and October are the best times to search for cheap Clearwater Beach vacation packages. Traveling in less busy months means you can generally find better prices on flights and hotels.

How many days is enough for Clearwater Beach?

With about 3 days, you'll have plenty of time to experience popular neighborhoods like Sand Key and Downtown Dunedin during your Clearwater Beach vacation. Remember to also add Sand Key Park and Beach Walk to your list of must-sees. Searching for more adventures? Consider exploring outside of Clearwater Beach on tours and day trips.

Is it worth booking a vacation package to Clearwater Beach?

Clearwater Beach has everything you need for a memorable getaway — coastal beaches, watersports and family-friendly attractions are just the start. Whether you want to check out attractions like Clearwater Marine Aquarium and Pier 60 Park, or take the road less traveled, you'll find plenty to experience on your Clearwater Beach vacation.

How to find the best Clearwater Beach package deals?

Bagging a cheap Clearwater Beach package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most affordable Clearwater Beach package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.

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

An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can tailor your Clearwater Beach trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.

When to book a vacation package to Clearwater Beach?

Land amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Clearwater Beach trip.

How to plan a trip to Clearwater Beach?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the type of activities available will also help you decide when to escape to Clearwater Beach.
  2. Budget wisely: As well as the price of your hotel, you should factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Clearwater Beach.
  3. Organize your Clearwater Beach getaway with Expedia's trip planning tool: Look for and book accommodations and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Clearwater Beach together.
  4. Decide how long to go away for: Now that you're up to speed on Clearwater Beach, you can work out the perfect length of your vacation. Create a draft plan and allocate enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Clearwater Beach vacation package.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on the best Clearwater Beach has to offer. Find all the exciting things to do in Clearwater Beach with our dedicated activity guide.

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

Set off on your dream getaway to Clearwater Beach with help from our Book Now, Pay Later vacations. No need to save up or wait for your next paycheck — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snag great deals before they disappear.

Book with confidence

Things to do in and around Clearwater Beach

Clearwater Beach is the perfect destination for a family-friendly outdoor vacation, offering a variety of activities. Enjoy stunning beach vacations, embark on exciting sea excursions, and explore hot springs. For adventure seekers, scuba diving tours are available, along with an activity guide to help you plan your days. Don't forget to visit the local resorts and shopping malls to make the most of your trip.

Shopping

For shopping in Clearwater Beach, visit The Amish Country Store, located 5 miles away, for unique gifts. Westfield Countryside Mall and Largo Mall, both 6 miles away, offer a variety of shops and entertainment options. If you're up for a drive, check out other nearby malls for more options.

Recreation

Experience the thrill of sports at BayCare Ballpark, just 6 miles from Clearwater Beach. Enjoy family fun and adventure at Captain Bligh’s Landing mini-golf. For a relaxing day outdoors, visit the Belleview Biltmore Golf Club, located 3 miles away, perfect for golf enthusiasts.

Adventure

At Celebration Station, located 6 miles from Clearwater Beach, enjoy thrilling arcade games and family-friendly attractions. SimCenter-Tampa-Bay-St-Petersburg-Clearwater.d6277317.Vacation-Attraction>SimCenter Tampa Bay, 4 miles away, offers immersive virtual experiences and arcade fun, while another SimCenter, also 6 miles away, provides exciting adventures for all ages in a vibrant setting.

Nightlife

Clearwater Beach nightlife is vibrant and lively, offering something for everyone. Enjoy beachfront bars like Shephard's Beach Resort for live music and dancing, or relax at Frenchy's Rockaway Grill for a laid-back vibe. Don’t miss the sunset celebrations at Pier 60 for entertainment and local vendors.

Find the best attractions in Clearwater Beach

Clearwater Beach, Florida, is an ideal destination for families and outdoor enthusiasts alike, offering beautiful beaches and urban parks. Visitors can enjoy the stunning Clearwater Beach and explore the iconic Clearwater Pier, along with nearby nature reserves. This vibrant area blends outdoor fun with a city experience, making it perfect for those looking to unwind or engage in various activities while soaking up the sun.

  • Clearwater Beach: Experience the quintessential beach vibes at Clearwater Beach, known for its soft, white sands and crystal-clear waters. Enjoy sunbathing, swimming, and a variety of water sports, making it a perfect spot for relaxation and fun.
  • Sand Key Park: This urban park offers a family-friendly atmosphere with expansive green spaces, picnic areas, and walking trails. Enjoy outdoor activities amid beautiful landscapes, making it an ideal spot for a family outing or a peaceful escape from the beach crowds.
  • Beach Walk: Stroll along this picturesque esplanade that beautifully connects the beach to local shops and eateries. With romantic views and family-friendly spots, Beach Walk is perfect for leisurely walks, sunset viewing, and enjoying the vibrant atmosphere.

Best time to go to Clearwater Beach

The best time to visit Clearwater 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 Clearwater 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 Clearwater 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.