Deals on vacations and trips to Holiday

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Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,351, price is now $717 per person
$717
per person
Dec 3 - Dec 10
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

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,825, price is now $1,531 per person
$1,531
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop 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.
Villa Valentino Luxury 8BR Villa & Pool

Villa Valentino Luxury 8BR Villa & Pool

3 out of 5
Allen's Ridge
Price was $5,409, price is now $3,136 per person
$3,136
per person
Jan 1 - Jan 4
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
An outdoor pool, free self parking, and laundry facilities are featured at this villa. WiFi in public areas is free. A terrace, a garden, and barbecue grills are also on offer.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,333, price is now $821 per person
$821
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip non-stop 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.
Residence Inn by Marriott Clearwater Downtown

Residence Inn by Marriott Clearwater Downtown

3 out of 5
Downtown Clearwater
Save 100% on your flight
Price was $1,257, price is now $794 per person
$794
per person
Dec 31 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Top Holiday hotels deals

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy, Tampa, FL
$144 nightly
The price is $163 total per night
$163 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

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Free Cancellation
Reserve now, pay when you stay
$215 nightly
The price is $242 total per night
$242 total
Nov 2 - Nov 3
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
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
3050 N Rocky Point Dr W, Tampa, FL
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $87 total per night
$87 total
Nov 23 - Nov 24
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
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive, Clearwater Beach, FL
Free Cancellation
Reserve now, pay when you stay
$244 nightly
The price is $276 total per night
$276 total
Oct 28 - Oct 29
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
Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

2.5 out of 5
650 Bay Esplanade, Clearwater Beach, FL
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $134 total per night
$134 total
Oct 30 - Oct 31
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
JW Marriott Clearwater Beach Resort & Spa

JW Marriott Clearwater Beach Resort & Spa

4 out of 5
691 S Gulfview Blvd, Clearwater Beach, FL
Free Cancellation
Reserve now, pay when you stay
$331 nightly
The price is $374 total per night
$374 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
Don't see what you're looking for?
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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.

Key Vista Nature Park

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 River Park

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.

Anclote Gulf Park

Frequently asked questions

How much are vacation packages to Holiday?
With vacation packages being sold for just $717, 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.

Photos of local treasures

Browse Holiday vacation photos for more inspiration

Photo by Travel Ginger
Photo by Travel Ginger
Photo by Jignesh Patel
Photo by Jignesh Patel

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