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.
The Beachcomber
Save 100% on your flight
Price was $728, price is now $505 per person
$505
per person
May 4 - May 8
found 2 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
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 rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,931, price is now $1,142 per person
$1,142
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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
Save 100% on your flight
Price was $1,692, price is now $1,105 per person
$1,105
per person
Jun 8 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $848, price is now $561 per person
$561
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,115, price is now $744 per person
$744
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 St. Armands Circle and Lido Beach are located nearby.
Plaza Beach Hotel Beachfront Resort
Save 100% on your flight
Price was $1,501, price is now $1,028 per person
$1,028
per person
Jun 8 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
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 rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto 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 ...
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 Salvador Dali Museum and Fort ...
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 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
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 ...
SureStay Hotel by Best Western St. Pete Clearwater Airport
Clearwater FL
23.71 km from Pine Key
Book a stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and 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
2.66 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 ...
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 ...
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 ...
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 ...
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 ...
Tropical Palms Hotel
3580 Ulmerton Rd Clearwater FL
23.43 km from Pine Key
Stay at this hotel in Clearwater. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
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 ...
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.
Mon, May 4 - Thu, May 21
TTN
Mercer
TPA
Tampa Intl.
$86 Roundtrip, found 2 hours ago
$86
Roundtrip
found 2 hours ago
Mon, May 25 - Thu, May 28
JFK
John F. Kennedy Intl.
TPA
Tampa Intl.
$177 Roundtrip, found 4 hours ago
$177
Roundtrip
found 4 hours ago
Sat, Jun 13 - Wed, Jun 24
SWF
Stewart Intl.
TPA
Tampa Intl.
$224 Roundtrip, found 4 days ago
$224
Roundtrip
found 4 days ago
Sat, Aug 15 - Wed, Sep 2
MSP
Minneapolis - St. Paul Intl.
SRQ
Sarasota-Bradenton Intl.
$239 Roundtrip, found 2 days ago
$239
Roundtrip
found 2 days ago
Wed, May 6 - Sat, May 16
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago