
Exclusive Pinellas Trail Vacation Deals

Pinellas Trail vacation package deals
Price found within the past 48 hours. Click for updated prices.

voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $1,057, price is now $635 per person
$635
per person
Jun 1 - Jun 8
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,227, price is now $749 per person
$749
per person
Jun 1 - Jun 8
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

Resort Sixty-Six
Save 100% on your flight
Price was $1,398, price is now $890 per person
$890
per person
May 16 - May 23
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
A restaurant and an outdoor pool are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

SkyBeach Resort
Greater Pinellas Point
Price was $1,645, price is now $1,056 per person
$1,056
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Relax with beach cabanas, sun loungers, and beach umbrellas. Traveling for business? Take advantage of the express check-in, express check-out, and conference space.

Captiva Beach Resort
South Village
Save 100% on your flight
Price was $1,158, price is now $746 per person
$746
per person
May 27 - Jun 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
A private beach and an outdoor pool are featured at this smoke-free condo. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.

DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto
Price was $1,786, price is now $1,155 per person
$1,155
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This hotel features 2 bars/lounges, a beach bar, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. You'll appreciate the outdoor pool, poolside bar, and concierge services.
Frequently asked questions
Top Pinellas Trail hotel deals

Casa de Corazon-A comfortable home with pool in a quiet neighborhood near beach.
Largo FL
This vacation home features an outdoor pool and a hot tub. WiFi in public areas is free. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
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.
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