Gateway Vacations from $301
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The Latest Gateway Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy
Save 100% on your flight
Price was $1,140, price is now $694 per person
$694
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (900 reviews)
Everyone is exceptionally nice except the front desk woman on the morning of Monday October 6th. Not very friendly. Bad mood.
Reviewed on Oct 6, 2025
Haley's at The Anna Maria Island Inn
Save 100% on your flight
Price was $780, price is now $476 per person
$476
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
8.6/10 Excellent! (375 reviews)
Very clean, newly remodeled. Only issues were the bathroom is teeny tiny! No room to move around in, at all. Can hardly sit on toilet. Shower door hits the sink. Also, the pull out couch was so new the plastic wrap was still on the mattress and we could not pull it out of the couch!! And could not get TV’s to work. That is why it received a rating of a 3.
Reviewed on Oct 22, 2025
Captiva Beach Resort
South Village
Save 100% on your flight
Price was $756, price is now $492 per person
$492
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (1,143 reviews)
Very good stay, clean, safe, and steps from the beach
Reviewed on Oct 25, 2025
The Retreat at Anna Maria Island Inn
Save 100% on your flight
Price was $726, price is now $480 per person
$480
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.2/10 Wonderful! (25 reviews)
Very clean suite. Customer service was excellent. Nicole V is excellent and so extremely helpful and friendly.
Reviewed on Oct 26, 2025
Where to stay in Gateway
Find the best Gateway areas and neighborhoods for the activities you enjoy most. Learn more about Gateway
South Venice
4/5(16 area reviews)
While visiting South Venice, you might make a stop by sights like Venice Area Audubon Society and Jacaranda West Country Club.
Gateway Hotel Deals
Motel 6 Venice, FL
281 US 41 Bypass North, Venice, FL
Fully refundableReserve now, pay when you stay
$56 nightly
The price is $63 total per night from Nov 9 to Nov 10
$63 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (325 reviews)
Clean room, i should have asked for the first floor, but didn't. Staff seemed nice
Reviewed on Oct 29, 2025
Ramada by Wyndham Venice Hotel Venezia
425 Us Highway 41 Byp N, Venice, FL
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $112 total per night from Nov 9 to Nov 10
$112 total
Nov 9 - Nov 10
Total with taxes and fees
7/10 Good! (1,009 reviews)
Friendly staff, great food
Reviewed on Oct 30, 2025
Hampton Inn & Suites Venice Bayside South Sarasota
881 Venetia Bay Blvd, Venice, FL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $135 total per night from Nov 30 to Dec 1
$135 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Room was clean and spacious.
Reviewed on Oct 30, 2025
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.
Discover the most popular places to visit in Gateway
Venice Beach
4.5/5(862 reviews)
Beachside bliss awaits at a Florida coastal gem where you can swim, fish and hunt for ancient fossils in the sand and beneath the waves.
Caspersen Beach
4.5/5(89 reviews)
If a restful vacation is part of your travel plans, Caspersen Beach might be the perfect place to seek out during your trip to Venice. Attend a sporting event in the area, or seek out the biking trails.
Manasota Beach
4.5/5(200 reviews)
Why not spend a carefree afternoon at Manasota Beach during your travels in Venice Island? Discover the sunsets while you're in the area.
Things to do
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
$55
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.