Holiday Vacations from $430

Book a Hotel + Flight or Car together to unlock savings

Photo by Travel Ginger

Your Holiday Vacation

Book a customized Holiday vacation package that has everything you need and nothing you don't. Great for shopping, walking and gift and craft shops, consider basing yourself in the neighborhood of Downtown Dunedin. If taking in sights is on the cards during your trip to Holiday, stop by leading attractions like Green Key Beach, Robert K Rees Memorial Park and James E. Grey Preserve. Whatever your travel plans or the size of your budget, putting together a tailored Holiday vacation is a walk in the park with Expedia.

The Latest Holiday vacation packages

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
Save 100% on your flight
Price was $728, price is now $430 per person
$430
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (618 reviews)
We were very pleased with our 3 night stay at the hotel. The staff graciously offered us an umbrella and chairs to take to the beach from the donation stash. We really appreciated that and returned the items when we left for future guests.

Reviewed on Sep 8, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $1,453, price is now $717 per person
$717
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,058 reviews)
Hands down one of the best hotels I’ve ever stayed at. Not only is it in a gorgeous location but the suite was incredible, the wine that was waiting for us in our room was phenomenal and the amenities were wonderful. They offer bikes for free as part of your stay, and me and my daughter biked all around the island it was such a good day ☀️. Would absolutely recommend this place to anybody. Perfect for couples but also very family friendly too. Will be staying here again!!

Reviewed on Sep 7, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $882, price is now $451 per person
$451
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,017 reviews)
Loved it Voco hotel was great clean and quiet great place to just sit back and relax place was not busy at all kids are all back in school thank god . Beach’s all near by 10 to 20 minute drive to any beach u wana go too.

Reviewed on Sep 2, 2025

Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $1,058, price is now $596 per person
$596
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (23 reviews)
I love the convenient location and a nice staff I'll be excited when the upgrades are done I can't wait to return in November

Reviewed on Sep 10, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,000, price is now $588 per person
$588
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,069 reviews)
$50 a night parking _ had no option

Reviewed on Sep 9, 2025

Don't see what you're looking for?
See all available trips from Singapore to Holiday
View all trips

Where to stay in Holiday

Find the best Holiday areas and neighborhoods for the activities you enjoy most. Learn more about Holiday
Default Image

Key Vista

If you're looking for some top things to see and do in Key Vista and surrounding area, you can visit Anclote River Park and Tarpon Springs Sponge Docks.

Find hotels in Key Vista

Discover the most popular places to visit in Holiday

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

What to do in Holiday

Tarpon Springs Train Depot at Night

Tarpon Springs: Ghost and Haunted History Tour

$40
per adult
Tarpon Springs: Ghost and Haunted History Tour
Goodacre's "Naiads" at the Sponge Docks

I Came, I Saw... I GREEKED!

$165
per adult
I Came, I Saw... I GREEKED!
2 Hours Kayak Eco Tour in Tarpon Springs

2 Hours Kayak Eco Tour in Tarpon Springs

$54
per adult
2 Hours Kayak Eco Tour in Tarpon Springs
See all activities in Holiday

Holiday Hotel Deals

Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive, Tampa, FL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $237 total per night from Sep 18 to Sep 19
$237 total
Sep 18 - Sep 19
Total with taxes and fees
8.8/10 Excellent! (1,051 reviews)
"very good"

Reviewed on Sep 9, 2025

Grand Hyatt Tampa Bay
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $231 total per night from Sep 21 to Sep 22
$231 total
Sep 21 - Sep 22
Total with taxes and fees
8/10 Very Good! (2,180 reviews)
"P"

Reviewed on Sep 10, 2025

Hilton Clearwater Beach Resort & Spa
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy, Tampa, FL
Fully refundable
$152 nightly
The price is $173 total per night from Sep 15 to Sep 16
$173 total
Sep 15 - Sep 16
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Everything was excellent. The fitness room was not open and was told to go to Double Tree."

Reviewed on Sep 10, 2025

The Westin Tampa Bay
See all 5,884 properties in Holiday
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Holiday vacation package cost?
You can pick up a vacation package to this destination from $430 on Expedia. But how much your vacation to Holiday costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Holiday?
If you're hoping to snag a cheap Holiday vacation package, consider visiting in May, June and July. You'll typically find lower prices on hotels and airfares during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Holiday?
Typically, a handful of days is enough for a Holiday vacation. With a well-organized itinerary, you can go to all the main attractions such as Anclote Gulf Park, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Holiday?
It's no wonder a Holiday vacation is on the to-do list of many travelers. Top attractions like Anclote River Park are just the start of what you can explore here.
How to find the best Holiday package deals?
Use Expedia's filter tool to find some tempting Holiday package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Holiday package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Holiday vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Holiday getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Holiday?
If you've got your Holiday travel dates finalized, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Holiday?

  1. Choose when to go: Check your schedule and get packing. Your favorite season and the type of activities on offer will also help you decide when to visit Holiday.
  2. Set a budget: Factor in expenses such as flights, transportation and food when calculating how much to put aside for your trip to Holiday. Then, choose a property that suits your budget, whether that's a wallet-friendly option or a lavish retreat.
  3. Explore Holiday with our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Holiday. You can also save your must-visit places, collaborate with friends and family and manage your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Holiday, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  5. Bundle your accommodations and airfare: After you've settled on your dates and duration, book the perfect Holiday vacation package for you.
  6. Book experiences or activities ahead of time: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on Holiday's highlights. Find all the exciting things to do in Holiday in Holiday with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Holiday vacation packages?
If you're like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Holiday trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.