Pine Key Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Pine Key Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort
Wesley Chapel South
Price was $1,065, price is now $420 per person
$420
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this spa resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
Courtyard by Marriott Tampa Oldsmar
Save 100% on your flight
Price was $724, price is now $515 per person
$515
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly hotel in Oldsmar. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Oldsmar Flea Market and Tampa Bay Downs are located nearby.
Residence Inn by Marriott Tampa Oldsmar
Save 100% on your flight
Price was $707, price is now $540 per person
$540
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly hotel in Oldsmar. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Oldsmar Flea Market and Tampa Bay Downs are located nearby.
SPOT X Hotel Tampa - Wesley Chapel by The Red Collection
Save 100% on your flight
Price was $673, price is now $518 per person
$518
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly hotel in Wesley Chapel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions KRATE Shopping Center and The Grove at Wesley Chapel are located nearby.
Ruskin Inn Hotel
Save 100% on your flight
Price was $541, price is now $432 per person
$432
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly hotel in Ruskin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Cypress Golf Club and Sun City Center Library are located nearby.
Fairfield Inn & Suites by Marriott Tampa Fairgrounds/Casino
Save 100% on your flight
Price was $790, price is now $657 per person
$657
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Seminole Hard Rock Casino Tampa and Busch Gardens Tampa Bay are located nearby.
Top Hotel Deals
Hilton St. Petersburg Bayfront
333 1st St S St. Petersburg FL
12.99 km from Pine Key
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful ...
RumFish Beach at TradeWinds
6000 Gulf Blvd St. Pete Beach FL
5.48 km from Pine Key
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 ...
Sirata St. Pete Beach
5300 Gulf Blvd St. Pete Beach FL
4.79 km from Pine Key
Book a stay at this beach resort in St. Pete Beach. Enjoy 2 outdoor pools, 3 restaurants, and a beach locale. Our guests praise the pool and the helpful staff ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
21.45 km from Pine Key
Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Sunset Vistas Two Bedroom Beachfront Suites
12000 Gulf Blvd Treasure Island FL
11.15 km from Pine Key
Book a stay at this beach condo in Treasure Island. Enjoy 2 outdoor pools, a beach locale, and 2 hot tubs. Our guests praise the pool and the helpful staff in ...
Hilton St. Petersburg Carillon Park
950 Lake Carillon Dr St. Petersburg FL
23.54 km from Pine Key
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
The Don CeSar
3400 Gulf Boulevard St. Pete Beach FL
2.66 km from Pine Key
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 ...
The Beachcomber
6200 Gulf Blvd St. Pete Beach FL
5.57 km from Pine Key
Book a stay at this beach hotel in St. Pete Beach. Enjoy 2 outdoor pools, a beach locale, and a nightclub. Our guests praise the helpful staff and the clean ...
Island Grand at TradeWinds
5500 Gulf Blvd St. Pete Beach FL
5.08 km from Pine Key
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 ...
Quality Inn Saint Petersburg North-Tampa Bay
2595 54th Ave N St. Petersburg FL
16.15 km from Pine Key
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Bilmar Beach Resort
10650 Gulf Blvd Treasure Island FL
9.98 km from Pine Key
Book a stay at this beach resort in Treasure Island. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms ...
GALAXY HOTEL
101 3rd Ave N St. Petersburg FL
13.5 km from Pine Key
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Popular attractions Tampa ...
Hollander Boutique Hotel
421 4th Ave N St. Petersburg FL
13.34 km from Pine Key
Book a stay at this spa hotel in St. Petersburg. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sun, Jan 18 - Sat, Jan 24
ORD
O'Hare Intl.
TPA
Tampa Intl.
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Tue, Jan 27 - Mon, Feb 2
LGA
LaGuardia
TPA
Tampa Intl.
$110 Roundtrip, found 12 hours ago
$110
Roundtrip
found 12 hours ago
Mon, Feb 2 - Fri, Feb 6
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Sat, Jan 10 - Sat, Jan 17
MSP
Minneapolis - St. Paul Intl.
SRQ
Sarasota-Bradenton Intl.
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago