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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.
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,483, price is now $954 per person
$954
per person
Mar 25 - Mar 30
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 4 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,981, price is now $1,097 per person
$1,097
per person
Apr 25 - May 3
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.
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $2,194, price is now $1,293 per person
$1,293
per person
Apr 25 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a rooftop terrace. 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.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Price was $1,718, price is now $1,017 per person
$1,017
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,884, price is now $1,136 per person
$1,136
per person
May 2 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Splash Island Water Park are located nearby.
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $2,630, price is now $1,744 per person
$1,744
per person
Apr 24 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk are located nearby.
The Don CeSar

The Don CeSar

4 out of 5
Save 100% on your flight
Price was $3,080, price is now $2,064 per person
$2,064
per person
May 2 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Fort De Soto Park and John's Pass Village & Boardwalk are located nearby.
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $3,269, price is now $2,243 per person
$2,243
per person
Mar 25 - Mar 30
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Sand Key Park are located nearby.

Oldsmar Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
BAY INN

BAY INN

2 out of 5
Temple Crest
Price was $511, price is now $354 per person
$354
per person
May 6 - May 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $772, price is now $524 per person
$524
per person
Apr 11 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,169, price is now $810 per person
$810
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Price was $578, price is now $402 per person
$402
per person
May 6 - May 10
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,082, price is now $653 per person
$653
per person
Apr 24 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $1,204, price is now $664 per person
$664
per person
Apr 8 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Price was $1,718, price is now $1,017 per person
$1,017
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,884, price is now $1,136 per person
$1,136
per person
May 2 - May 9
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
Sun, May 3 - Thu, May 7
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$76 Roundtrip, found 11 hours ago
$76
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sun, May 3 from Philadelphia Intl. to Tampa Intl., returning Thu, May 7, priced at $76 found 11 hours ago
Frontier Airlines
Mon, Apr 13 - Thu, Apr 16
TTN
Mercer
TPA
Tampa Intl.
$78 Roundtrip, found 11 hours ago
$78
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Apr 13 from Mercer to Tampa Intl., returning Thu, Apr 16, priced at $78 found 11 hours ago
Frontier Airlines
Wed, May 13 - Wed, May 13
CLE
Hopkins Intl.
TPA
Tampa Intl.
$88 Roundtrip, found 8 hours ago
$88
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, May 13 from Hopkins Intl. to Tampa Intl., returning Wed, May 13, priced at $88 found 8 hours ago
Frontier Airlines
Sun, May 10 - Mon, May 18
ORD
O'Hare Intl.
TPA
Tampa Intl.
$98 Roundtrip, found 16 hours ago
$98
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sun, May 10 from O'Hare Intl. to Tampa Intl., returning Mon, May 18, priced at $98 found 16 hours ago