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Legacy Trail Vacation Packages

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Legacy Trail Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $375, price is now $253 per person
$253
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $2,274, price is now $1,290 per person
$1,290
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Bean Point Beach are located nearby.

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $650, price is now $391 per person
$391
per person
Oct 21 - Oct 24
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $740, price is now $460 per person
$460
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $606, price is now $382 per person
$382
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
We loved this unique, well run hotel. Everyone was helpful and fun to talk to. Jake at check-in was great. The room was lovely and clean and the location was outstanding.

Reviewed on Jul 31, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $644, price is now $410 per person
$410
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
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 in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
The room was nice

Reviewed on Aug 1, 2026

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $871, price is now $558 per person
$558
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
The room was more like a small apartment! Plenty of space for our family of 5. The staff was friendly. Very clean facility. Convenient location. We will definitely stay here again.

Reviewed on Jul 30, 2026

CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $523, price is now $336 per person
$336
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Everything was great

Reviewed on Jul 31, 2026

Legacy Trail Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $314, price is now $210 per person
$210
per person
Sep 5 - Sep 8
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,014, price is now $588 per person
$588
per person
Sep 5 - Sep 8
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $650, price is now $391 per person
$391
per person
Oct 21 - Oct 24
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $623, price is now $379 per person
$379
per person
Oct 21 - Oct 24
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)

Legacy Trail Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $1,370, price is now $675 per person
$675
per person
Sep 12 - Sep 19
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $2,274, price is now $1,290 per person
$1,290
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,301, price is now $752 per person
$752
per person
Sep 12 - Sep 19
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,145, price is now $1,263 per person
$1,263
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Allegiant Air
Thu, Aug 27 - Sun, Aug 30
PSM
Portsmouth Intl.
PGD
Punta Gorda Airport
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Aug 27 from Portsmouth Intl. to Punta Gorda Airport, returning Sun, Aug 30, priced at $122 found 1 day ago
Delta
Tue, Nov 3 - Tue, Nov 10
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$209 Roundtrip, found 5 hours ago
$209
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Nov 3 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Tue, Nov 10, priced at $209 found 5 hours ago
Delta
Tue, Sep 29 - Sun, Oct 4
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$212 Roundtrip, found 2 hours ago
$212
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Sep 29 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Sun, Oct 4, priced at $212 found 2 hours ago
United
Tue, Sep 1 - Wed, Sep 2
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 1 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 2, priced at $220 found 1 day ago