Holiday Vacation Packages 2026 from $657

Holiday flight + hotel vacation packages

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

BeachTrail Lodging

Save 100% on your flight

$657

per person

Sep 30 - Oct 6

found 1 day ago

Roundtrip flight included

New York (NYC) to Tampa (TPA)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace and laundry facilities are also provided.

Ocean Club Treasure Island Hotel

Sunshine Beach

$1,130

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.

CW Hotel

Save 100% on your flight

$884

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,263

per person

Sep 1 - Sep 7

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

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

The Hotel Zamora

Save 100% on your flight

$791

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

A marina, a 24-hour gym, and a restaurant are all featured at this Mediterranean hotel. Unwind with a drink at one of the 3 bars/lounges and enjoy freebies like WiFi in public areas and a beach shuttle. You'll appreciate the outdoor pool, poolside bar, and concierge services.

Top Holiday hotels deals

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$260 nightly

$294 total

Aug 2 - Aug 3

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.

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$163 total

Aug 23 - Aug 24

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.

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$214 nightly

$242 total

Aug 9 - Aug 10

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.

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$225 nightly

$254 total

Aug 9 - Aug 10

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.

Grand Hyatt Tampa Bay

2900 Bayport Drive Tampa FL

Free Cancellation

Reserve now, pay when you stay

$201 nightly

$228 total

Jul 26 - Jul 27

Total with taxes and fees

This smoke-free hotel features 2 restaurants, 2 outdoor pools, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. There's a bar/lounge on site, and concierge services and wedding services are also provided.

Clearwater Beach Sheraton Resort on Sand Key

1160 Gulf Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$243 nightly

$274 total

Aug 16 - Aug 17

Total with taxes and fees

This smoke-free resort includes 2 restaurants, an outdoor pool, and a 24-hour gym. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.

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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 $657, 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.