Holiday Vacation Packages 2026 from $428

Holiday flight + hotel vacation packages

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

The Fold Hotels Indian Shores

Save 100% on your flight

$428

per person

Nov 7 - Nov 11

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A business center, a terrace, and laundry facilities are also on offer.

Crystal Palms Beach Resort

Sunshine Beach

Save 100% on your flight

$752

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a hot tub. Dry cleaning, laundry facilities, and barbecue grills are also on offer.

Seaside at Anna Maria Island Inn

Save 100% on your flight

$1,969

per person

Dec 14 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Tampa (TPA)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box.

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,407

per person

Dec 14 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Tampa (TPA)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

St Pete Beach Suites

$696

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

Top Holiday hotels deals

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$250 nightly

$283 total

Oct 28 - Oct 29

Total with taxes and fees

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, express check-out, and valet parking. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Pool

Hot Tub

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$281 nightly

$317 total

Oct 1 - Oct 2

Total with taxes and fees

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this resort. Families will appreciate the children's pool and onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Hot Tub

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

$206 nightly

$233 total

Oct 12 - Oct 13

Total with taxes and fees

This resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor pools and perks like free WiFi.

On private beach

Pool

Fairfield Inn & Suites by Marriott Clearwater Beach

650 Bay Esplanade Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$138 total

Oct 27 - Oct 28

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the free continental breakfast each morning.

Pool

Breakfast included

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL

$163 nightly

$185 total

Oct 25 - Oct 26

Total with taxes and fees

A private beach, a 24-hour gym, and a restaurant are all featured at this hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the outdoor pool and perks like free WiFi.

On private beach

Pool

Opal Sands Resort

430 South Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$324 nightly

$366 total

Oct 4 - Oct 5

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury resort. Make the most of the gym and hot tub, and relax with drinks at one of the 2 bars/lounges.

Pool

Hot Tub

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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.

Stay near popular Holiday attractions

A calm body of water with a sailboat, a distant shoreline, and a clear sky.

Anclote River Park

8.8/10 (48 reviews)

Why not spend a carefree afternoon at Anclote River Park during your travels in Holiday? While you're in the area, wander around the parks.

See properties

Frequently asked questions

How much are vacation packages to Holiday?

With vacation packages being sold for just $428, you won't need to empty your piggy bank for your visit to Holiday. Travelocity can help. Bundle your flights, hotels and experiences into a package and score some serious discounts. The more you book, the more you save.

How long should my Holiday vacation be?

Typically, 2 nights is what most travelers book for their Holiday trip. That's an useful guide, but there's so much more to discover if you give yourself a little longer.

Where can I get the best vacation package deals for Holiday?

It's difficult to beat Travelocity when it comes to putting together your Holiday package deal. There are as many as 400 partner airlines and 1,000,000 worldwide properties to choose from. Secure your trip now and get ready to tick another exciting place off your bucket list.

Why should I book my Holiday vacation bundle with Travelocity?

With first-rate service, customer support available 24/7 and some of the most perfect escapes money can buy, you'll never wander alone. And if you find a better price, we'll match it. That's our Price Match Guarantee.

Can I save money on my Holiday car rental if I combine it with my hotel or flight?

With a Holiday vacation package, you can bundle your flight, car and hotel bookings and save a tidy sum. If you can't wait to see the best of this fantastic region, why not make tracks to Universal Studios Florida? This famous attraction is 80 mi from Holiday. With your own set of wheels, you'll be there belong long.

What is the best time of year to go to Holiday?

If you're all about wandering wisely, is the perfect time to do it. That's when hotel rates are at their cheapest. In contrast, prices surge around . January, February and September are the most popular times for a vacation in Holiday, so expect big lines at major tourist sites. Prefer to avoid high season? You'll find smaller crowds in May, June and July.

Which airport is best for Holiday?

Tampa Intl. Airport (TPA) (19 mi away from downtown), Sarasota-Bradenton Intl. Airport (SRQ) (55 mi away from central Holiday) and St. Petersburg-Clearwater Intl. Airport (PIE) (19 mi away from central Holiday) are all great options for Holiday.

What is there to do in Holiday?

You'll notice a certain magic as you stroll the streets of Holiday. Anclote River Park and Key Vista Nature Park are just two famous attractions that make this city such a sought-after destination, so put them at the top of your itinerary.

Where should I stay when visiting Holiday?

Many travelers choose to spend their nights at the Holiday Hotel. It's an excellent base for your Holiday getaway.