Oyster Bay Vacations from ￥58,716

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    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

The Latest Oyster Bay Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
San Jose (SJC) to Tampa (TPA)
9.2/10 Wonderful! (1,027 reviews)
Decent Dated: bath tub instead of walk in shower Elevator is slow Not bad

Reviewed on Jun 29, 2025

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
San Jose (SJC) to Sarasota (SRQ)
8.8/10 Excellent! (1,945 reviews)
Staff was friendly and very nice, food was good but pricey; prepare to pay for parking

Reviewed on Jun 29, 2025

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
San Jose (SJC) to Sarasota (SRQ)
8.4/10 Very Good! (2,266 reviews)
The hotel shuttle is great. Gets you to restaurants, Tampa General.

Reviewed on Jun 30, 2025

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
San Jose (SJC) to Sarasota (SRQ)
7/10 Good! (1,527 reviews)
Somewhat nice. The view of the river is pretty. I hate that they told me they sold out of our room so they gave me a cheaper option (they did give me a free drink) the only other issue is there’s a required fee for riding a bike, and a dinner credit. I didn’t once use it and still got charged.

Reviewed on Jun 26, 2025

The Royale 2B 4B Luxury Garden Pool Yoga Room

The Royale 2B 4B Luxury Garden Pool Yoga Room

2 out of 5
Golfview
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
San Jose (SJC) to Sarasota (SRQ)
No reviews

Where to stay in Oyster Bay

Find the best Oyster Bay areas and neighborhoods for the activities you enjoy most. Learn more about Oyster Bay
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South Sarasota

While visiting South Sarasota, you might make a stop by sights like The Landings and Coconuts Family Entertainment Center.

Find hotels in South Sarasota

Oyster Bay Hotel Deals

Kompose Boutique Hotel
Kompose Boutique Hotel
3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (4,041 reviews)
"Shower floor with some kind of soft material loved it easy on my feet"

Reviewed on Jun 29, 2025

Get rates
Kompose Boutique Hotel
Tropical Beach Resorts
Tropical Beach Resorts
3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is ￥28,156 per night from Jul 2 to Jul 3
￥28,156
￥35,086 total
Jul 2 - Jul 3
includes taxes & fees
9.2/10 Wonderful! (4,728 reviews)
"We had a wonderful stay at Tropical Beach Resorts! This is a nice, family-like resort that truly makes you feel at home from the moment you arrive. The location is great—just a 2-minute walk to the beach, and only 5 minutes walking distance to local restaurants, shops, and cafes. The staff was amazing ..."

Reviewed on Jun 24, 2025

Tropical Beach Resorts
Compass Hotel by Margaritaville Anna Maria Sound
Compass Hotel by Margaritaville Anna Maria Sound
4 out of 5
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
The price is ￥25,395 per night from Jul 6 to Jul 7
￥25,395
￥32,259 total
Jul 6 - Jul 7
includes taxes & fees
9.4/10 Exceptional! (1,514 reviews)
"Great hotel"

Reviewed on Jun 27, 2025

Compass Hotel by Margaritaville Anna Maria Sound
See all 12,532 properties in Oyster Bay
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 does an Oyster Bay vacation package cost?
Much less than you might think --- from a tempting ￥58,716, actually! By combining flights, hotels and car rentals into your own custom-made package, your Oyster Bay escape is just clicks away.
How do I get a cheap travel package to Oyster Bay?
Browse and lock in everything in the one place with our Oyster Bay vacation packages. You'll find bargains on flights, hotels and more that'll keep your travel budget happy and your spirit of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options across the globe to pick from, you'll have endless opportunities to mix and match however you please.
Where should I stay in Oyster Bay?
Take the hassle out of sightseeing by staying in a hotel right around the corner from Oyster Bay's biggest attractions. St. Armands Circle and Mote Marine Laboratory & Aquarium are two which top many visitors' bucket lists.
How far in advance should I book my Oyster Bay vacation?
Savvy travelers often book as early as possible. You can normally look up international airfares on Expedia up to 12 months before your intended flight. If you're booking last minute, don't worry. Bargain prices occasionally become available just weeks prior to departure.
What does an Expedia Oyster Bay travel package include?
With Expedia, you can choose any combination of hotels, flights and car rentals to build your perfect Oyster Bay package. Once you've made your booking, you can add on the fun stuff like sightseeing tours and activities. Don't forget --- the more you bundle, the more cash you'll save!
What should I know before booking an Oyster Bay travel package?
Bundling your bookings into an Oyster Bay vacation package is the easiest way to organize your trip. Not only that, you'll get great discounts just for combining your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with an Oyster Bay Expedia vacation package?
Yes, you're in charge. Expedia has access to more than 550 airlines across the globe, so you can design your Oyster Bay trip according to your style and budget.
If I'm not able to travel, can I cancel my Oyster Bay vacation package?
Because we know life can throw you a few curveballs, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you've booked your Oyster Bay vacation package in the last 24 hours, you may be able to change or cancel it free of charge. Your hotel, airline or car rental company may impose a fee if your booking is older than that.

Discover the most popular places to visit in Oyster Bay

Mall at University Town Center

Mall at University Town Center

4.5/5(363 reviews)

You can search for that perfect souvenir at Mall at University Town Center during your visit to Sarasota. Attend a sporting event or discover the beautiful sunsets in this family-friendly area.

Mall at University Town Center
Sarasota Classic Car Museum featuring heritage elements and interior views

Sarasota Classic Car Museum

1/5(1 review)

With rare vintage makes, classic models and a large range of collectibles, this car museum is a popular attraction for motoring enthusiasts and the car-curious.

Sarasota Classic Car Museum

University of South Florida Sarasota

4.5/5(58 reviews)

Take a campus tour or just explore the area of University of South Florida Sarasota, during your trip to Sarasota. In the area, take in the fascinating museums and beautiful sunsets.

University of South Florida Sarasota

Things to do

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

￥7,953
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
HydroCats

HydroCats - 2 Hour CraigCat Sightseeing Tour

￥21,080
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

￥14,315
per adult
Anna Maria Island & Bradenton Beach Parasailing Tour
See all activities in Sarasota
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.