Oyster Bay Holidays

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Your Oyster Bay Holiday

Book an Oyster Bay holiday package and immerse yourself in the way of life and rhythm of this fascinating neighbourhood. With all your travel plans worked out, the only thing you need to concentrate on here is having a great time. Not sure where to go during your trip to Oyster Bay? Nearby attractions such as Siesta Key Beach, Marie Selby Botanical Gardens and Lido Beach are excellent places to start. Expedia can help you turn your ideal Oyster Bay holiday into reality, whatever your travel plans or budget.

Our guide on 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
A sandy beach path with people walking, a wooden fence, and a clear blue sky with clouds.

Lido Key

Traverse a winding woodland path and spend the afternoon on this island’s secluded beaches before ending at a beachside bar to enjoy a spectacular sunset.

Find hotels in Lido Key
A cityscape with a mix of modern and historic buildings, palm trees, and a cloudy sky.

South Sarasota

Though South Sarasota may not have many top sights, you can venture to the surrounding area to see attractions like Siesta Key Beach and The Landings.

Find hotels in South Sarasota
A waterfront with palm trees, a dock, and a clear blue sky.

Central Sarasota

1 out of top 10 points of interest in this area

Gardens, art galleries and theatres highlight some of the noteworthy features of Central Sarasota. Make a stop by Sarasota Opera House or Marina Jack while you're exploring the neighbourhood.

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A wooden pier extending into a body of water with a cloudy sky above.

Downtown Sarasota

While visiting Downtown Sarasota, you might make a stop by sights like Sarasota Opera House and Regal Hollywood - Sarasota.

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A beach with clear water, rocks, and a sunset.

Palmer Ranch

While there might not be top attractions in Palmer Ranch, you can explore the larger area and discover places like Stoneybrook Golf & Country Club and Turtle Beach.

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Our pick of the best Oyster Bay Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
AU$92
27 Oct - 28 Oct
includes taxes & fees
9.2/10 Wonderful! (6,074 reviews)
"Clean room, helpful staff, beautiful property"

Reviewed on 1 Oct 2026

Kompose Boutique Hotel
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
AU$260
1 Nov - 2 Nov
includes taxes & fees
Compass Hotel by Margaritaville Anna Maria Sound
Tropical Beach Resorts

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
AU$257
4 Oct - 5 Oct
includes taxes & fees
9.4/10 Exceptional! (5,932 reviews)
"Everything to me was wonderful. From the front desk to the cleaning crew, everyone we spoke to were so welcoming and courteous. The white beach sand is so impressive with the water at a very short walking distance, I can’t ask for more. My wife and I will definitely be back!"

Reviewed on 1 Oct 2026

Tropical Beach Resorts
See all 13,833 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.
All Inclusive Holidays
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beach holidays
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Golf Holidays
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Spa Holidays

Frequently asked questions

How much does an Oyster Bay holiday package cost?
Much less than you might think — from a tempting , 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 holiday 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 holiday?
Savvy travellers 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 holiday package is the easiest way to organise 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 holiday 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 holiday 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 holiday 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.

Activities

Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

AU$77
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

AU$153
per adult
100% of travellers recommend
Anna Maria Island & Bradenton Beach Parasailing Tour
Manatee Discovery Anna Maria Island

Manatee Discovery Anna Maria Island

AU$77
per adult
Manatee Discovery Anna Maria Island
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.