Oldsmar Vacations

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Find the Best Oldsmar Vacation Packages

Oldsmar Hotel Deals

Wyndham Grand Clearwater Beach
Wyndham Grand Clearwater Beach
4 out of 5
100 Coronado Drive, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is AED 1,451 per night from May 4 to May 5
AED 1,451
AED 1,768 total
includes taxes & fees
4 May - 5 May
9.2/10 Wonderful! (2,061 reviews)
"Had a great family vacation at this hotel. Bunk beds for the kids was cool. The only complaints are that the food from room service is garbage & people lay their towels on the chairs around the pool to hold their spot. Management should stop that from happening as there are ZERO chairs after 8am ..."

Reviewed on 3 April 2025

Wyndham Grand Clearwater Beach
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
The price is AED 933 per night from Apr 20 to Apr 21
AED 933
AED 1,200 total
includes taxes & fees
20 Apr - 21 Apr
7.8/10 Good! (1,788 reviews)
Will be back!
"Great stay! The valet attendants are friendly. The front desk staff is always on top of things. I will say that for almost $500/night I wish I couldn't hear my neighbors alarm going off at 4am due to thinner walls…but that is my only negative comment I have. I love staying here."

Reviewed on 2 April 2025

Hilton Clearwater Beach Resort & Spa
Ramada by Wyndham Tampa Westshore Airport South
Ramada by Wyndham Tampa Westshore Airport South
3 out of 5
1200 N Westshore Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is AED 418 per night from Apr 6 to Apr 7
AED 418
AED 471 total
includes taxes & fees
6 Apr - 7 Apr
6/10 (3,035 reviews)
"We stayed for one night and it wasn’t too bad. Hotel does offer free continental breakfast and water. Pool needed a better filter, but it got the job done for the time we were there. The front desk staff were amazing. It was also walking distance to a few restaurants ie longhorn, Ruth Chris, Olive ..."

Reviewed on 31 March 2025

Ramada by Wyndham Tampa Westshore Airport South
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.

Frequently asked questions

How much does an Oldsmar vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Oldsmar costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Oldsmar?
If you’re looking to snag a cheap Oldsmar vacation package, consider visiting in September, October and November. You’ll generally find lower rates on flights and hotels during these quieter months — perfect for travelers wishing to save money.
How to find the best Oldsmar package deals?
Start your search for an Oldsmar package deal by entering your travel dates and destination under our “Packages” tab. Then add some filters, like “Property type” and “Guest rating,” to tailor the results to your exact style. You can also sort by “Package discount” and discover offers that come with unbeatable savings. If you don’t find the perfect Oldsmar package deal straight away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oldsmar getaway off to a flying start.
Is it cheaper to book an Oldsmar vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging stays and flights separately. Better still, you can tailor your Oldsmar getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Oldsmar?
If you’ve got your Oldsmar travel dates locked in, book as early as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Oldsmar?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Oldsmar.
  2. Plan your budget wisely: On top of the price of your hotel, you’ll need to factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Oldsmar.
  3. Decide how long to go for: Now that you’re up to speed on Oldsmar, you can work out the ideal length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that’s left is to pick an Oldsmar vacation package that brings all your bookings together.

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