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
$826
per person
Nov 17 - Nov 25
found 3 hours ago
Roundtrip non-stop flight included
Billings (BIL) 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.
CW Resort
$1,071
per person
Nov 17 - Nov 25
found 3 hours ago
Roundtrip non-stop flight included
Billings (BIL) 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.
We could not have asked for more. CW resort is located in a perfect spot rught by a quiet marina and a short walk to pier 60 as well as walgreens. The property is taken care of and new. The pool has salt water and was always clean. It was very convenient having an in-house restaurant when we didn't want to go far. All the staff were friendly and helpful. Our family hopes to return!
Reviewed on Oct 3, 2026
Innisbrook Resort
$891
per person
Nov 17 - Nov 25
found 3 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Tampa (TPA)
Book a stay at this spa resort in Palm Harbor. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Innisbrook Golf Club and Leepa-Rattner Museum of Art are located nearby.
Wyndham Grand Clearwater Beach
$1,222
per person
Nov 17 - Nov 25
found 3 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Tampa (TPA)
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
Edge Hotel Clearwater Beach
$1,017
per person
Nov 17 - Nov 25
found 3 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Tampa (TPA)
Book a stay at this business-friendly hotel in Clearwater Beach. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. Popular attractions Pier 60 Park and Sand Key Park are located nearby.
ChartHouse Clearwater Beach Marina Hotel
$1,058
per person
Nov 17 - Nov 25
found 3 hours ago
Roundtrip non-stop flight included
Billings (BIL) 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.
Top Hotel Deals
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 ...
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 ...
Extended Stay America Suites Clearwater Carillon Park
2311 Ulmerton Rd Clearwater FL
Book a stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
GALAXY HOTEL
101 3rd Ave N St. Petersburg FL
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Popular attractions Tampa ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 Salvador ...
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 ...
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, Dec 13 - Mon, Dec 21
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$94
Roundtrip
found 3 days ago
Tue, Nov 3 - Tue, Nov 10
BOS
Logan Intl.
TPA
Tampa Intl.
$179
Roundtrip
found 1 hour ago
Sat, Nov 14 - Wed, Nov 25
MSP
Minneapolis - St. Paul Intl.
TPA
Tampa Intl.
$227
Roundtrip
found 3 days ago
Sun, Oct 11 - Sat, Nov 14
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$397
Roundtrip
found 2 days ago
Sat, Feb 20 - Sat, Mar 6
PHL
Philadelphia Intl.
SRQ
Sarasota-Bradenton Intl.
$424
Roundtrip
found 3 days ago
Best points of interest in St. Petersburg - Clearwater
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