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.
ChartHouse Clearwater Beach Marina Hotel
Price was $803, price is now $661 per person
$661
per person
Jul 30 - Aug 3
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Island Grand at TradeWinds
Price was $1,008, price is now $790 per person
$790
per person
Jul 30 - Aug 3
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
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 in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.
RumFish Beach at TradeWinds
Price was $878, price is now $695 per person
$695
per person
Jul 30 - Aug 3
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
The Don CeSar
Save 100% on your flight
Price was $1,302, price is now $1,041 per person
$1,041
per person
Jul 30 - Aug 3
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
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 in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.
Clearwater Beach Sheraton Resort on Sand Key
Sand Key
Price was $836, price is now $675 per person
$675
per person
Jul 30 - Aug 3
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Book a stay at this beach resort in Clearwater Beach. Enjoy 2 restaurants, a beach locale, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Hyatt Regency Clearwater Beach Resort and Suites
Price was $1,075, price is now $872 per person
$872
per person
Jul 30 - Aug 3
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Book a stay at this beach resort in Clearwater Beach. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Top Hotel Deals
RumFish Beach at TradeWinds
6000 Gulf Blvd St. Pete Beach FL
5.43 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 ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
21.46 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 ...
Island Grand at TradeWinds
5500 Gulf Blvd St. Pete Beach FL
5.07 km from Pine Key
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 ...
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 ...
Sirata Beach Resort St Pete Beach
5300 Gulf Boulevard St. Pete Beach FL
4.76 km from Pine Key
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 ...
The Don CeSar
3400 Gulf Boulevard St. Pete Beach FL
2.73 km from Pine Key
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 ...
SkyBeach Resort
6800 Sunshine Skyway Lane St. Petersburg FL
5.36 km from Pine Key
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Pass-a-Grille Beach and Upham ...
Bilmar Beach Resort
10650 Gulf Blvd Treasure Island FL
9.99 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 ...
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 ...
Hyatt Place St. Petersburg / Downtown
25 2nd Street North St. Petersburg FL
13.22 km from Pine Key
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 ...
Mint House St. Petersburg Downtown by Kasa
77 11th St N St. Petersburg FL
12.27 km from Pine Key
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
12.09 km from Pine Key
Stay at this hotel in St. Petersburg. Enjoy free WiFi, 3 restaurants, and 3 bars/lounges. Popular attractions Salvador Dali Museum and Vinoy Park are located ...
Treasure Island Hotel and Marina
11125 Gulf Blvd Treasure Island FL
10.4 km from Pine Key
Book a stay at this business-friendly hotel in Treasure Island. Enjoy free WiFi, a marina, and a rooftop terrace. Our guests praise the helpful staff and the ...
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.
Sat, Sep 26 - Thu, Oct 1
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$96 Roundtrip, found 5 days ago
$96
Roundtrip
found 5 days ago
Tue, Aug 18 - Tue, Sep 1
JFK
John F. Kennedy Intl.
TPA
Tampa Intl.
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Wed, Sep 9 - Sat, Sep 19
EWR
Newark Liberty Intl. Airport
TPA
Tampa Intl.
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Tue, Sep 22 - Wed, Sep 23
ORD
O'Hare Intl.
TPA
Tampa Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Tue, Jul 28 - Mon, Aug 10
MDW
Midway Intl.
TPA
Tampa Intl.
$200 Roundtrip, found 5 days ago
$200
Roundtrip
found 5 days ago