Holiday Vacation Packages 2025/2026 from $440

Holiday flight + hotel vacation packages

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

Bayview Plaza Waterfront Resort

Belle Vista

$440

per person

Jan 5 - Jan 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

A marina and an outdoor pool are featured at this smoke-free hotel. Spend a day at the beach kayaking, or relax with beach cabanas and sun loungers. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities.

The Avalon Club

$905

per person

Jan 14 - Jan 18

found 24 hours 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.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$475

per person

Dec 7 - Dec 12

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.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$545

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

New Hotel Collection Harbourside

Save 100% on your flight

$497

per person

Jan 17 - Jan 22

found 10 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

A rooftop terrace, free self parking, and laundry facilities are featured at this hotel. A coffee shop, a terrace, and concierge services are also on offer.

Top Holiday hotels deals

The Westin Tampa Bay

7627 W Courtney Campbell Cswy, Tampa, FL

Free Cancellation

$135 nightly

$153 total

Nov 23 - Nov 24

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

$215 nightly

$242 total

Nov 17 - Nov 18

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

Wyndham Grand Clearwater Beach

100 Coronado Drive, Clearwater Beach, FL

$217 nightly

$245 total

Dec 1 - Dec 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

Grand Hyatt Tampa Bay

2900 Bayport Drive, Tampa, FL

Free Cancellation

Reserve now, pay when you stay

$224 nightly

$254 total

Nov 23 - Nov 24

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

DoubleTree by Hilton Tampa Rocky Point Waterfront

3050 N Rocky Point Dr W, Tampa, FL

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$87 total

Nov 30 - Dec 1

Total with taxes and fees

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

Pool

Pet friendly

JW Marriott Clearwater Beach Resort & Spa

691 S Gulfview Blvd, Clearwater Beach, FL

Free Cancellation

Reserve now, pay when you stay

$334 nightly

$377 total

Nov 19 - Nov 20

Total with taxes and fees

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the 24-hour gym and visit the 2 bars/lounges and poolside bar for drinks.

Pool

Spa

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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 $440, 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.