Deals on vacations and trips to Legacy Trail

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Legacy Trail flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $822, price is now $516 per person
$516
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $973, price is now $605 per person
$605
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,021, price is now $670 per person
$670
per person
Sep 25 - Sep 28
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,120, price is now $744 per person
$744
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, express check-out, and valet parking. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,072, price is now $716 per person
$716
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Top Legacy Trail hotels deals

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Free Cancellation
Reserve now, pay when you stay
$187 nightly
The price is $210 total per night
$210 total
Aug 3 - Aug 4
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Free Cancellation
Reserve now, pay when you stay
$137 nightly
The price is $154 total per night
$154 total
Aug 10 - Aug 11
Total with taxes and fees
This smoke-free aparthotel features 3 restaurants, 6 outdoor pools, and 10 outdoor tennis courts. There's fun for all ages with a free kid's club and mini golf, and barbecue grills are available on site. Enjoy the 8 hot tubs and perks like free WiFi.
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
4441 Collins Avenue Miami Beach FL
Free Cancellation
Reserve now, pay when you stay
$388 nightly
The price is $442 total per night
$442 total
Jul 21 - Jul 22
Total with taxes and fees
This luxury hotel features a full-service spa, a nightclub, and 9 restaurants. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy the 4 outdoor pools and gym.
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Free Cancellation
$98 nightly
The price is $110 total per night
$110 total
Aug 9 - Aug 10
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Loews Miami Beach Hotel – South Beach

Loews Miami Beach Hotel – South Beach

4.5 out of 5
1601 Collins Ave Miami Beach FL
Free Cancellation
Reserve now, pay when you stay
$229 nightly
The price is $261 total per night
$261 total
Jul 22 - Jul 23
Total with taxes and fees
A full-service spa, 4 restaurants, and 2 hot tubs are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-out, and valet parking. You'll appreciate the outdoor pool, bar/lounge, and limo/town car service.
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Miracle Strip Parkway Southeast, 1500 Fort Walton Beach FL
$187 nightly
The price is $210 total per night
$210 total
Aug 19 - Aug 20
Total with taxes and fees
This resort features 3 restaurants, 2 outdoor pools, and a hot tub. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
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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.

Frequently asked questions

How much are vacation packages to Legacy Trail?
Let Travelocity take the worry out of arranging your visit to Legacy Trail. Check out our fabulous $516 package deal and save both time and money. With your hotel and flights locked in, you can channel your energy into planning the fun parts of your escape — like getting to those must-do attractions!
Where can I get the best vacation package deals for Legacy Trail?
Travelocity can help you find a Legacy Trail package deal. With more than 400 airlines and 1,000,000 properties around the world, there's no doubt you'll be able to put together the perfect itinerary.
Why should I book my Legacy Trail vacation package with Travelocity?
Whether you're searching for the ultimate unplugged getaway or you crave the hustle and bustle of the big city, booking everything with Travelocity saves you time, money and hassle. No need to search through hundreds of different websites to find the best deal — our Price Match Guarantee ensures you'll always score the lowest possible price, and our team of customer service experts are available round-the-clock.

Photos of local treasures

Browse Legacy Trail vacation photos for more inspiration

A wooden pathway surrounded by dense greenery and trees.
A rural road flanked by dense tropical vegetation and palm trees.
A paved road flanked by dense tropical vegetation.
A large indoor auditorium with tiered seating, a stage, and a balcony.

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