Search Deals onGateway Vacation Packages
Gateway Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy
Save 100% on your flight
Price was $801, price is now $538 per person
$538
per person
May 6 - May 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this golf hotel in Bradenton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Longboat Key Beaches and Coquina Beach are located nearby.
Captiva Beach Resort
South Village
Save 100% on your flight
Price was $909, price is now $597 per person
$597
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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.
SeaSpray Resort
Save 100% on your flight
Price was $1,219, price is now $844 per person
$844
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this aparthotel in Siesta Key. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Save 100% on your flight
Price was $1,396, price is now $1,009 per person
$1,009
per person
May 24 - May 31
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Punta Gorda Airport (PGD)
Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Siesta Key Inn
South Village
Save 100% on your flight
Price was $783, price is now $591 per person
$591
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Compass Hotel by Margaritaville Anna Maria Sound
Save 100% on your flight
Price was $1,089, price is now $839 per person
$839
per person
May 6 - May 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
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 Bradenton Beach and Coquina Beach are located nearby.
Tropical Breeze Resort
Siesta Key Village
Save 100% on your flight
Price was $1,897, price is now $1,470 per person
$1,470
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Siesta Heron Suites & Villas
Save 100% on your flight
Price was $906, price is now $708 per person
$708
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this vacation home in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Turtle Beach are located nearby.
3-4 Night Vacations in Gateway
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Gateway
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Gateway
Ramada by Wyndham Venice Hotel Venezia
425 Us Highway 41 Byp N Venice FL
Book a stay at this business-friendly hotel in Venice. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff in our ...
Motel 6 Venice, FL
281 US 41 Bypass North Venice FL
Stay at this motel in Venice. Enjoy free WiFi, free parking, and 10 beach bars. Our guests praise the helpful staff in our reviews. Popular attractions Venice ...
Hampton Inn & Suites Venice Bayside South Sarasota
881 Venetia Bay Blvd Venice FL
Book a stay at this business-friendly hotel in Venice. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Save an average of 15% on thousands of hotels when you're signed in
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Book a stay at this beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in ...
Carlisle Inn
3727 Bahia Vista Sarasota FL
Stay at this hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Spark by Hilton Sarasota Siesta Key Gateway
6600 S Tamiami Trl Sarasota FL
Book a stay at this business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff ...
Lido Beach Resort
700 Benjamin Franklin Dr Sarasota FL
Book a stay at this beach resort in Sarasota. Enjoy free WiFi, 2 outdoor pools, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
Tropical Breeze Resort
140 Columbus Blvd. Siesta Key FL
Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Apr 11 - Sat, Apr 25
PHL
Philadelphia Intl.
SRQ
Sarasota-Bradenton Intl.
$82 Roundtrip, found 2 hours ago
$82
Roundtrip
found 2 hours ago
Sun, Apr 19 - Sat, May 2
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$207 Roundtrip, found 16 hours ago
$207
Roundtrip
found 16 hours ago
Wed, May 6 - Mon, May 11
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$207 Roundtrip, found 23 hours ago
$207
Roundtrip
found 23 hours ago
Mon, May 25 - Tue, Jun 9
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$211 Roundtrip, found 20 hours ago
$211
Roundtrip
found 20 hours ago
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