Holiday Vacation Packages 2026 from $1,023

Holiday flight + hotel vacation packages

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

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,023

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 Resort

Save 100% on your flight

$1,240

per person

Jan 1 - Jan 8

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 gym and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.

Cedar Cove Resort and Cottages

$1,053

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip non-stop 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 picnic area are also on offer.

voco Sarasota by IHG

Central Sarasota

$1,401

per person

Dec 27 - Jan 3

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, along with express check-out. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Landing St. Petersburg Near South Branch Potomac River

Save 100% on your flight

$1,677

per person

Dec 23 - Dec 30

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. Enjoy the a rooftop terrace and perks like free self parking and free WiFi. Dry cleaning, barbecue grills, and a virtual front desk are also on offer.

Top Holiday hotels deals

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$272 nightly

$307 total

Nov 15 - Nov 16

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

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$297 nightly

$335 total

Nov 17 - Nov 18

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.

Pool

Hot Tub

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$176 total

Oct 25 - Oct 26

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.

On private beach

Pool

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$198 nightly

$224 total

Nov 8 - Nov 9

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

Fairfield Inn & Suites by Marriott Clearwater Beach

650 Bay Esplanade Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$153 total

Nov 10 - Nov 11

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the free continental breakfast each morning.

Pool

Breakfast included

Gulfview Hotel on the Beach

625 S Gulfview Blvd Clearwater Beach FL

$144 nightly

$162 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, luggage storage, and laundry facilities are also on offer.

Pool

Hot Tub

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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 $1,023, 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.