Deals on vacations and trips to Holiday

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Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $824, price is now $510 per person
$510
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Tampa (TPA)
This resort features a golf course, a full-service spa, and 3 restaurants. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy the 2 outdoor pools and perks like free WiFi.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $2,766, price is now $1,566 per person
$1,566
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,734, price is now $1,562 per person
$1,562
per person
Mar 1 - Mar 7
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
A private beach and an outdoor pool are featured at this hotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site.
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Save 100% on your flight
Price was $1,465, price is now $931 per person
$931
per person
Mar 1 - Mar 8
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
A marina and an outdoor pool are featured at this smoke-free hotel. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the gym and perks like free WiFi.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $836, price is now $533 per person
$533
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.

Top Holiday hotels deals

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
$241 nightly
The price is $272 total per night
$272 total
Jan 4 - Jan 5, 2026
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
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
$190 nightly
The price is $215 total per night
$215 total
Jan 11 - Jan 12, 2026
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
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Free Cancellation
$143 nightly
The price is $163 total per night
$163 total
Dec 23 - Dec 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
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive Tampa FL
Free Cancellation
Reserve now, pay when you stay
$224 nightly
The price is $254 total per night
$254 total
Dec 21 - Dec 22
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

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
$130 nightly
The price is $148 total per night
$148 total
Dec 25 - Dec 26
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
Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
301 S Gulfview Blvd Clearwater Beach FL
Free Cancellation
Reserve now, pay when you stay
$279 nightly
The price is $315 total per night
$315 total
Dec 24 - Dec 25
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this 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
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 $510, 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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