Search Deals onGateway Vacation Packages
Gateway Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland
Price was $610, price is now $530 per person
$530
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this hotel in Osprey. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Nokomis Beach and Turtle Beach are located nearby.
The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Save 100% on your flight
Price was $2,524, price is now $1,624 per person
$1,624
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach hotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Escape Coastal Resort on Casey Key
Price was $948, price is now $768 per person
$768
per person
May 26 - May 30
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Stay at this hotel in Nokomis. Enjoy free WiFi, a marina, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Nokomis Beach and Venice Beach are located nearby.
Landing Palmetto Apartments
Price was $811, price is now $675 per person
$675
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Book a stay at this luxury aparthotel in Palmetto. Enjoy free WiFi, free parking, and 2 outdoor pickleball courts. Popular attractions Moccasin Wallow Golf Club and Andersen Race Park are located nearby.
Bradenton Apartments by Landing
Price was $1,038, price is now $865 per person
$865
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Book a stay at this luxury aparthotel in Bradenton. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Coquina Beach and IMG Bollettieri Tennis Academy are located nearby.
Palmetto Marriott Resort & Spa
Price was $801, price is now $691 per person
$691
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this luxury hotel in Palmetto. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Popular attractions Manatee County Agricultural Museum and Riverwalk are located nearby.
Casey Key Resorts - Beachfront
Price was $1,073, price is now $963 per person
$963
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach hotel in Nokomis. Enjoy free WiFi, free parking, and a private beach. Popular attractions Nokomis Beach and Venice Beach are located nearby.
Tradewinds Beach Resort
Price was $958, price is now $873 per person
$873
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this condo in Bradenton Beach. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and Bradenton 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
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 ...
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 ...
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 ...
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 ...
The Westin Sarasota
100 Marina View Drive Sarasota FL
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 ...
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.
Mon, May 4 - Sat, May 16
PHL
Philadelphia Intl.
SRQ
Sarasota-Bradenton Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Tue, May 12 - Sat, May 16
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Tue, May 19 - Wed, Jun 3
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$202 Roundtrip, found 3 days ago
$202
Roundtrip
found 3 days ago
Wed, May 6 - Sat, May 16
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
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