Oyster Bay Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Top hotels in Oyster Bay

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
The price is ฿2,492 per night from 23 Nov to 24 Nov
฿2,492
฿3,542 total
23 Nov - 24 Nov
includes taxes & fees
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 ฿4,987 per night from 3 Nov to 4 Nov
฿4,987
฿6,512 total
3 Nov - 4 Nov
includes taxes & fees
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 ฿5,179 per night from 29 Nov to 30 Nov
฿5,179
฿6,805 total
29 Nov - 30 Nov
includes taxes & fees
9.4/10 Exceptional! (2,645 reviews)
"Our room was very clean and modern. The front desk, bartender and each employee we encountered were polite, friendly and helpful. Breakfast was very good. We loved the bar area and took our drinks outside to sit in the patio area. We will definitely be back. The hotels’ location to Anna Maria beaches ..."

Reviewed on 28 Oct 2026

Compass Hotel by Margaritaville Anna Maria Sound
See all 14,030 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 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.

Things to do

Lido Key: Self-Guided Paddleboard Rental

Lido Key: Self-Guided Paddleboard Rental

฿1,429
per adult
100% of travellers recommend
Lido Key: Self-Guided Paddleboard Rental
Anna Maria Island: The Island Kayak Tour

Anna Maria Island: The Island Kayak Tour

฿2,170
per adult
100% of travellers recommend
Anna Maria Island: The Island Kayak Tour
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

฿2,170
per adult
86% of travellers recommend
Siesta Key, FL - Clear Kayak LED Night Glass Bottom 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.