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Oldsmar Vacation Packages

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Oldsmar Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Tampa Fairgrounds/Casino

Wyndham Garden Tampa Fairgrounds/Casino

2 out of 5
Save 100% on your flight
Price was $439, price is now $286 per person
$286
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Tampa. Enjoy free parking, breakfast (surcharge), and a fitness center. Popular attractions Seminole Hard Rock Casino Tampa and Busch Gardens Tampa Bay are located nearby.
Very clean rooms. Excellent rates. Friendly staff.

Reviewed on Sep 25, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,454, price is now $909 per person
$909
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.
It was very comfortable. I love the fact you have transportation to go to the beach and that you gave us the umbrella, towels and chairs. The front desk personnel were very nice and helpful. Thanks

Reviewed on Sep 23, 2026

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,085, price is now $707 per person
$707
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this golf hotel in Bradenton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and IMG Bollettieri Tennis Academy are located nearby.
Excelente

Reviewed on Sep 25, 2026

St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Save 100% on your flight
Price was $1,516, price is now $991 per person
$991
per person
Dec 10 - Dec 13
found 9 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Stay at this motel in St. Pete Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Upham Beach are located nearby.

The Knickerbocker by Delphius

The Knickerbocker by Delphius

3 out of 5
Save 100% on your flight
Price was $970, price is now $636 per person
$636
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this business-friendly B&B in Tampa. Enjoy free WiFi, free parking, and 3 meeting rooms. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.

The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $1,352, price is now $896 per person
$896
per person
Nov 9 - Nov 15
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,412, price is now $949 per person
$949
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Our family had a wonderful stay. The location was perfect. We also loved being able to use the hotels umbrellas, chairs & towels at the beach. The suite was more spacious than we expected! The sofa bed was not comfortable, but the regular beds were. Can’t beat the price for the room & view we had. We would absolutely come back!

Reviewed on Sep 21, 2026

VIinoy House

VIinoy House

3.5 out of 5
Save 100% on your flight
Price was $1,230, price is now $826 per person
$826
per person
Nov 9 - Nov 15
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this B&B in St. Petersburg. Enjoy free WiFi, free parking, and bathrobes. Popular attractions Tampa Bay and Vinoy Park are located nearby.

Oldsmar Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Tampa Fairgrounds/Casino

Wyndham Garden Tampa Fairgrounds/Casino

2 out of 5
Save 100% on your flight
Price was $439, price is now $286 per person
$286
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,491, price is now $966 per person
$966
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Save 100% on your flight
Price was $1,516, price is now $991 per person
$991
per person
Dec 10 - Dec 13
found 9 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
The Knickerbocker by Delphius

The Knickerbocker by Delphius

3 out of 5
Hyde Park
Save 100% on your flight
Price was $970, price is now $636 per person
$636
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)

Oldsmar Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $919, price is now $515 per person
$515
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Residence Inn By Marriott Tampa Downtown

Residence Inn By Marriott Tampa Downtown

3 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,229, price is now $672 per person
$672
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,161, price is now $1,242 per person
$1,242
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,589, price is now $935 per person
$935
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Nov 17 - Wed, Dec 2
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$106 Roundtrip, found 1 hour ago
$106
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Philadelphia Intl. to Tampa Intl., returning Wed, Dec 2, priced at $106 found 1 hour ago
Allegiant Air
Fri, Oct 30 - Mon, Nov 2
PHL
Philadelphia Intl.
PIE
St. Petersburg-Clearwater Intl.
$108 Roundtrip, found 6 days ago
$108
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Oct 30 from Philadelphia Intl. to St. Petersburg-Clearwater Intl., returning Mon, Nov 2, priced at $108 found 6 days ago
Frontier Airlines
Mon, Oct 26 - Fri, Oct 30
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Oct 26 from Detroit Metropolitan Wayne County to Tampa Intl., returning Fri, Oct 30, priced at $112 found 1 day ago
Allegiant Air
Sun, Oct 18 - Thu, Nov 5
TTN
Mercer
PIE
St. Petersburg-Clearwater Intl.
$125 Roundtrip, found 2 days ago
$125
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Sun, Oct 18 from Mercer to St. Petersburg-Clearwater Intl., returning Thu, Nov 5, priced at $125 found 2 days ago