Search Deals onOldsmar Vacation Packages
Oldsmar Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $578, price is now $342 per person
$342
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bean Point Beach and Anna Maria Beach are located nearby.
Loved this property. Perfect place for a quiet vacation. Sits right on the beach and the views were amazing. The owner and staff were very nice. Booked through Expedia and it was a little expensive but would stay there again.
Reviewed on Jul 17, 2026
ChartHouse Clearwater Beach Marina Hotel
Price was $704, price is now $350 per person
$350
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
CW Hotel
Price was $1,353, price is now $717 per person
$717
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!
Reviewed on Jul 8, 2026
Wyndham Grand Clearwater Beach
Save 100% on your flight
Price was $1,581, price is now $997 per person
$997
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $795, price is now $504 per person
$504
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Really enjoyed staying at Hibiscus Suites. It was really close to events we had planned as well as restaurants and Siesta Key Beach. Even though hotel is located on busy street, the traffic was not heard from room. I would highly recommend staying.
Reviewed on Jul 17, 2026
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $780, price is now $498 per person
$498
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Innisbrook Resort
Save 100% on your flight
Price was $635, price is now $418 per person
$418
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this spa resort in Palm Harbor. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Tarpon Springs Sponge Docks and Innisbrook Golf Club are located nearby.
So there is a serious bug problem. I think doors need to be replaced to prevent bugs. Roaches and beetles were in our room. Not ok.
Reviewed on Jul 7, 2026
DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto
Save 100% on your flight
Price was $1,174, price is now $775 per person
$775
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in North Redington Beach. Enjoy a beach locale, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Petersburg - Clearwater Beaches and John's Pass Village & Boardwalk are located nearby.
Great time at the property for a family of four (two teenagers). We had a room with ocean view, greatly recommend as it makes a difference to enjoy the stay. Will come back to this hotel. Great location, good restaurants nearby.
Reviewed on Jul 17, 2026
Oldsmar Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Oldsmar Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sun, Oct 18 - Thu, Nov 5
TTN
Mercer
PIE
St. Petersburg-Clearwater Intl.
$78 Roundtrip, found 9 hours ago
$78
Roundtrip
found 9 hours ago
Sun, Oct 4 - Thu, Oct 22
TTN
Mercer
TPA
Tampa Intl.
$86 Roundtrip, found 3 hours ago
$86
Roundtrip
found 3 hours ago
Thu, Oct 15 - Thu, Nov 5
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$86 Roundtrip, found 3 hours ago
$86
Roundtrip
found 3 hours ago
Mon, Oct 19 - Fri, Oct 30
CLE
Hopkins Intl.
TPA
Tampa Intl.
$103 Roundtrip, found 6 hours ago
$103
Roundtrip
found 6 hours ago
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