Search Deals onOldsmar Vacation Packages
Oldsmar Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel
Price was $752, price is now $502 per person
$502
per person
Dec 31 - Jan 4
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 Pier 60 Park and Clearwater Beach are located nearby.
Clean rooms, helpful staff, clean property. Balcony was nice too.
Reviewed on Nov 15, 2026
Hibiscus Suites - Gateway to Siesta Key
Price was $1,249, price is now $750 per person
$750
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip 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.
CW Resort
Price was $1,611, price is now $992 per person
$992
per person
Dec 31 - Jan 4
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 Pier 60 Park and Clearwater Beach are located nearby.
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $1,767, price is now $1,110 per person
$1,110
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Crystal Palms Beach Resort
Price was $1,251, price is now $795 per person
$795
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy a 24-hour front desk, dry cleaning or laundry services, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating
Reviewed on Nov 7, 2026
The Roth Hotel
Price was $813, price is now $527 per person
$527
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Treasure Island. Enjoy free WiFi, free parking, and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Sunset Beach Pavilion are located nearby.
Truly a treasure!!! Don’t miss the opportunity to stay here. Love the proximity to the beach. The dock was so tranquil and great for sipping coffee in the mornings and my son loved to fish and watch for dolphins & manatees!
Reviewed on Sep 12, 2026
The Avalon Club
Price was $1,578, price is now $1,042 per person
$1,042
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this aparthotel in Clearwater Beach. Enjoy a fitness center, parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Abode Beach House
Price was $825, price is now $559 per person
$559
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Pier 60 Park and Sand Key Park are located nearby.
Very nice rooms with a full small kitchenette. Everything was clean & the vibe was just perfect for my little 3 day getaway. Staff was friendly and helpful. Will visit again and will be recommending to my friends :-)
Reviewed on Nov 13, 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.
Mon, Jan 11 - Fri, Jan 15
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Mon, Jan 11 - Fri, Jan 15
PHL
Philadelphia Intl.
PIE
St. Petersburg-Clearwater Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Sun, Jan 10 - Thu, Jan 14
TTN
Mercer
PIE
St. Petersburg-Clearwater Intl.
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Wed, Feb 3 - Thu, Feb 4
CLE
Hopkins Intl.
TPA
Tampa Intl.
$84 Roundtrip, found 15 hours ago
$84
Roundtrip
found 15 hours ago
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