Holiday Vacation Packages 2026 from $420

Name: The Westin Tampa Bay
Price range: $167 total

Holiday flight + hotel vacation packages

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

Mar Bay Motel &Suites

Save 100% on your flight

$420

per person

Aug 17 - Aug 22

found 1 day ago

Roundtrip flight included

New York (LGA) to Tampa (TPA)

This hotel 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 an off-leash area. A garden, a library, and a picnic area are also on offer.

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$525

per person

Sep 2 - Sep 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.

CW Hotel

Save 100% on your flight

$689

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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

$560

per person

Sep 12 - Sep 15

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 Don CeSar

Save 100% on your flight

$862

per person

Sep 13 - Sep 16

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this historic resort. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families will appreciate the children's club, onsite laundry facilities, and babysitting.

Top Holiday hotels deals

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

$258 nightly

$292 total

Jul 8 - Jul 9

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

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$227 nightly

$256 total

Jul 6 - Jul 7

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

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$257 nightly

$290 total

Jul 28 - Jul 29

Total with taxes and fees

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

Pool

Hot Tub

Opal Sands Resort

430 South Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$424 nightly

$479 total

Jul 1 - Jul 2

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

Clearwater Beach Sheraton Resort on Sand Key

1160 Gulf Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$264 nightly

$299 total

Jul 6 - Jul 7

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.

Pool

Hot Tub

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$167 total

Jul 30 - Jul 31

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. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.

On private beach

Pet friendly

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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.

Popular places to visit

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

Anclote River Park

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.

A sandy beach with dense green foliage and calm waters.

Key Vista Nature Park

Commune with nature and explore the great outdoors at Key Vista Nature Park during your travels in Holiday. Stroll along the waterfront in this family-friendly area, or seek out the golf courses.

Anclote Gulf Park

Anclote Gulf Park is just one of the places to see in Holiday, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's waterfront, or seek out the golf courses.

Frequently asked questions

How much are vacation packages to Holiday?

With vacation packages being sold for just $420, 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.