Holiday Vacation Packages 2025/2026 from $448

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

$448

per person

Oct 13 - Oct 20

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.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$536

per person

Oct 28 - Nov 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

FUSION Resort Waterfront Suites

Save 100% on your flight

$679

per person

Oct 13 - Oct 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and perks like free self parking and free WiFi. A 24-hour business center, luggage storage, and concierge services are also on offer.

Ocean Club Treasure Island Hotel

Save 100% on your flight

$1,024

per person

Nov 1 - Nov 8

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.

Clearwater Suites

Save 100% on your flight

$568

per person

Oct 13 - Oct 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

An outdoor pool, self parking, and laundry facilities are featured at this hotel. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Holiday hotels deals

Grand Hyatt Tampa Bay

2900 Bayport Drive, Tampa, FL

Free Cancellation

Reserve now, pay when you stay

$200 nightly

$227 total

Aug 31 - Sep 1

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 valet parking. There's a bar/lounge on site, and concierge services and wedding services are also provided.

Pool

Pet friendly

The Westin Tampa Bay

7627 W Courtney Campbell Cswy, Tampa, FL

Free Cancellation

$161 nightly

$182 total

Sep 5 - Sep 6

Total with taxes and fees

A private beach, a 24-hour gym, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

On private beach

Pet friendly

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave, Clearwater Beach, FL

Free Cancellation

Reserve now, pay when you stay

$204 nightly

$231 total

Sep 1 - Sep 2

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 & Spa

301 S Gulfview Blvd, Clearwater Beach, FL

$234 nightly

$264 total

Sep 6 - Sep 7

Total with taxes and fees

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this eco-certified 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

Wyndham Grand Clearwater Beach

100 Coronado Drive, Clearwater Beach, FL

Free Cancellation

Reserve now, pay when you stay

$286 nightly

$323 total

Sep 1 - Sep 2

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

Gulfview Hotel on the Beach

625 S Gulfview Blvd, Clearwater Beach, FL

$95 nightly

$108 total

Sep 7 - Sep 8

Total with taxes and fees

A private beach and an outdoor pool are featured at this smoke-free hotel. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, luggage storage, and laundry facilities are also on offer.

On private beach

Pool

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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 beautiful beaches 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 $448, 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.