Holiday Vacation Packages 2025 from $450

Holiday flight + hotel vacation packages

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

Kompose Boutique Hotel

Save 100% on your flight

per person

May 1 - May 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Mar Bay Motel &Suites

Save 100% on your flight

per person

May 1 - May 7

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

May 12 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

The Avalon Club

Save 100% on your flight

per person

May 1 - May 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Island Grand at TradeWinds

Save 100% on your flight

per person

May 11 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

2 restaurants, 5 outdoor pools, and 2 hot tubs are among this resort's featured amenities. Dine at the beachfront restaurant and relax with free beach cabanas. Bring the family and enjoy the children's club, mini golf, and children's pool.

Top Holiday hotels deals

Rodeway Inn

2337 US Highway 19, Holiday, FL

Free Cancellation

Reserve now, pay when you stay

$100

includes taxes & fees

$89 per night

Apr 2 - Apr 3

Free self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. A garden is also provided.

Parking included

Free WiFi

Wyndham Grand Clearwater Beach

100 Coronado Drive, Clearwater Beach, FL

Free Cancellation

Reserve now, pay when you stay

$532

includes taxes & fees

$475 per night

Apr 2 - Apr 3

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

$350

includes taxes & fees

$310 per night

Apr 21 - Apr 22

This hotel 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. There's fun for all ages with a children's club and a playground, and families will appreciate the onsite laundry facilities.

On private beach

Pool

Sailport Waterfront Suites

2506 N Rocky Point Dr, Tampa, FL

$193

includes taxes & fees

$173 per night

Apr 30 - May 1

This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. You'll appreciate the gym, poolside bar, and snack bar/deli.

Pool

Kitchen

AC Hotel Clearwater Beach

395 Coronado Drive, Clearwater Beach, FL

Free Cancellation

Reserve now, pay when you stay

$249

includes taxes & fees

$220 per night

Apr 27 - Apr 28

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. There's a gym on site, and a 24-hour front desk and a rooftop terrace are also provided.

Pool

Pet friendly

Shephard's Beach Resort

619 S Gulfview Blvd, Clearwater Beach, FL

Free Cancellation

Reserve now, pay when you stay

$385

includes taxes & fees

$344 per night

Apr 8 - Apr 9

This hotel features 3 restaurants and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free valet parking. A coffee shop, a snack bar/deli, and a grocery/convenience store are also on offer.

Pool

Parking included

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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

Lovely isolated spot with white sands and Gulf waters as far as the eye can see #wanderlust #Florida

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 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.

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 $450, 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.