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.
Hibiscus Suites - Gateway to Siesta Key
$528
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Clean, organized room, good service, and good location!
Reviewed on Aug 18, 2026
Cedar Cove Resort and Cottages
$1,534
per person
Oct 1 - Oct 8
found 3 hours ago
Roundtrip flight included
Cincinnati (CVG) 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 Coquina Beach and Manatee Public Beach are located nearby.
The room we were staying in was simple, had 1 window out to the back and the parking lot of the property, it doesnt have any ocean view directly from that room. I think thats important to know. The property has other rooms with direct view to the Gulf which is fyi. The property is well kept, clean, simple and friendly. The beach is spectacular, very quiet, not crowded at all, the ocean was unbelievable clear and beautiful. Anna Maria is a dream to visit with many restaurants on the water
Reviewed on Aug 18, 2026
Captiva Beach Resort
South Village
$633
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
The proximity to the beach and the ambient of the place
Reviewed on Aug 17, 2026
Saddlebrook Resort
Wesley Chapel South
$775
per person
Oct 1 - Oct 8
just found
Roundtrip non-stop flight included
Cincinnati (CVG) to Tampa (TPA)
Book a stay at this golf resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
The front desk staff valet and transportation crew were great the property was so beautiful on the outside After weather delays traveling from Chicago to Tampa we finally made it to Saddlebrook about 1am Friday morning 2 roaches in the second bedroom spotted at 2 am 1 in the first spotted at 7 am we notified the fron desk we came back to the property about 2
Reviewed on Aug 18, 2026
SkyBeach Resort
Greater Pinellas Point
$805
per person
Oct 1 - Oct 8
just found
Roundtrip non-stop flight included
Cincinnati (CVG) to Tampa (TPA)
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Tropicana Field and Fort De Soto Park are located nearby.
Top Hotel Deals
Island Grand at TradeWinds
5500 Gulf Blvd St. Pete Beach FL
Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 5 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
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 ...
The Don CeSar
3400 Gulf Boulevard St. Pete Beach FL
Book a stay at this beach resort in St. Pete Beach. Enjoy a full-service spa, 2 restaurants, and a beach locale. Our guests praise the pool and the helpful staff ...
RumFish Beach at TradeWinds
6000 Gulf Blvd St. Pete Beach FL
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 Resort, Tapestry Collection by Hilton
5300 Gulf Boulevard St. Pete Beach FL
Book a stay at this beach hotel in St. Pete Beach. Enjoy an outdoor pool, a beach locale, and breakfast (surcharge). Popular attractions John's Pass Village ...
SkyBeach Resort
6800 Sunshine Skyway Lane St. Petersburg FL
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Tropicana Field and Fort De ...
Hilton St. Petersburg Bayfront
333 1st St S St. Petersburg FL
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 ...
Hollander Boutique Hotel
421 4th Ave N St. Petersburg FL
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. ...
The Beachcomber
6200 Gulf Blvd St. Pete Beach FL
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 ...
Bilmar Beach Resort
10650 Gulf Blvd Treasure Island FL
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 ...
Mint House St. Petersburg Downtown by Kasa
77 11th St N St. Petersburg FL
Book a stay at this business-friendly aparthotel in St. Petersburg. Enjoy free WiFi, valet parking (surcharge), and a picnic area. Our guests praise the helpful ...
Moxy St. Petersburg Downtown
1234 Central Avenue St. Petersburg FL
Stay at this hotel in St. Petersburg. Enjoy free WiFi, 3 restaurants, and 3 bars/lounges. Popular attractions Tropicana Field and Salvador Dali Museum are located ...
Barefoot Beach Club
13238 Gulf Blvd Madeira Beach FL
Book a stay at this beach hotel in Madeira Beach. Enjoy 2 outdoor pools, a beach locale, and a fitness center. Our guests praise the pool and the helpful staff ...
Plaza Beach Hotel Beachfront Resort
4506 Gulf Blvd St. Pete Beach FL
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean ...
Hyatt Place St. Petersburg / Downtown
25 2nd Street North St. Petersburg FL
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast ...
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, Oct 25 - Thu, Nov 12
TTN
Mercer
TPA
Tampa Intl.
$78
Roundtrip
found 6 days ago
Wed, Jan 6 - Tue, Jan 26
ORD
O'Hare Intl.
TPA
Tampa Intl.
$155
Roundtrip
found 5 days ago
Sat, Sep 19 - Sat, Sep 26
JFK
John F. Kennedy Intl.
TPA
Tampa Intl.
$169
Roundtrip
found 1 hour ago
Wed, Jan 6 - Tue, Jan 26
MDW
Midway Intl.
TPA
Tampa Intl.
$176
Roundtrip
found 5 days ago
Sat, Sep 12 - Sat, Sep 19
SWF
Stewart Intl.
TPA
Tampa Intl.
$179
Roundtrip
just found
Best points of interest in St. Petersburg - Clearwater
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