Legacy Trail Vacation Packages for 2026
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Legacy Trail Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Via Roma Beach Resort
$796
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Book a stay at this beach aparthotel in Bradenton Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Cortez Beach and Bradenton Beach are located nearby.
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Reviewed on Jul 18, 2026
Cedar Cove Resort and Cottages
$988
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Had an amazing time. Clean rooms, friendly staff. Amazing amenities with having use of beach chairs and umbrellas. Will return next summer.
Reviewed on Aug 13, 2026
Seaside at Anna Maria Island Inn
$1,783
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Book a stay at this beach hotel in Bradenton Beach. Enjoy a beach locale, daily housekeeping, and cable TV channels. Popular attractions Coquina Beach and Bradenton Beach are located nearby.
Anna Maria Beach Resort
$1,607
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.
Todo bien
Reviewed on Aug 13, 2026
Bali Hai Beachfront Resort and Spa
$1,127
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.
We loved this resort! You could not get closer to the beach. We had a pool view room and it still only took about 2 minutes to walk from our door to the sand. The resort is beautiful! Loved the pool area with lounge beds, TVs, cabanas, corn hole, and plenty of chairs. The complementary beach chairs and umbrellas were an amazing surprise! We were offered champagne at check in. There is a little restaurant and bar by the pool for coffee, lunch, and frozen drinks. The room was basically a small apartment with a kitchen, bedroom, and bathroom. I would definitely stay here again!
Reviewed on Aug 12, 2026
Tropic Isle at Anna Maria Island Inn
$870
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Stay at this hotel in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and Cortez Beach are located nearby.
It was very clean and in a great location!
Reviewed on Aug 12, 2026
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Rosen Inn Lake Buena Vista
8442 Palm Parkway Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Fontainebleau Miami Beach
4441 Collins Avenue Miami Beach FL
Book a stay at this luxury hotel in Miami Beach. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Loews Miami Beach Hotel – South Beach
1601 Collins Ave Miami Beach FL
Book a stay at this luxury hotel in Miami Beach. Enjoy a full-service spa, 4 restaurants, and a beach locale. Our guests praise the breakfast and the pool in ...
Walt Disney World Swan
1200 Epcot Resort Blvd Lake Buena Vista FL
Book a stay at this beach resort in Lake Buena Vista. Enjoy free WiFi, a private beach, and 3 hot tubs. Our guests praise the pool and the helpful staff in our ...
B Ocean Resort Fort Lauderdale Beach
1140 Seabreeze Blvd Fort Lauderdale FL
Book a stay at this beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the pool and the helpful staff ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Walt Disney World Dolphin
1500 Epcot Resort Blvd Lake Buena Vista FL
Book a stay at this beach hotel in Lake Buena Vista. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant ...
Eden Roc Miami Beach
4525 Collins Ave Miami Beach FL
Book a stay at this luxury resort in Miami Beach. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the bar in our ...
Holiday Inn Miami - International Airport by IHG
1111 S Royal Poinciana Blvd Miami Springs FL
Book a stay at this business-friendly hotel in Miami Springs. Enjoy free WiFi, a free airport shuttle, and 24-hour room service. Our guests praise the restaurant ...
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ...
The Island Resort at Fort Walton Beach
Miracle Strip Parkway Southeast, 1500 Fort Walton Beach FL
Book a stay at this beach resort in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool in our ...
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
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 ...
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.
Tue, Oct 20 - Wed, Oct 28
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$186
Roundtrip
found 23 hours ago
Tue, Nov 3 - Wed, Nov 18
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$219
Roundtrip
found 15 hours ago
Tue, Jan 5 - Tue, Jan 26
DTW
Detroit Metropolitan Wayne County
SRQ
Sarasota-Bradenton Intl.
$227
Roundtrip
found 16 hours ago
Tue, Nov 3 - Wed, Nov 18
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$229
Roundtrip
found 15 hours ago
Wed, Sep 16 - Wed, Oct 7
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$277
Roundtrip
found 10 hours ago
Best neighborhoods in Legacy Trail
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