Oyster Bay Vacations from $855

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Your Oyster Bay Vacation

Book an Oyster Bay vacation package and immerse yourself in the way of life and rhythm of this fascinating neighborhood. 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 vacation into reality, whatever your travel plans or budget.

The Latest Oyster Bay Vacation Packages

Price found within the past 48 hours. Click for updated prices.

The Fold Hotels Indian Shores

Save 100% on your flight

$855

per person

Nov 14 - Nov 21

found 1 day ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

9.2/10 Wonderful! (1,014 reviews)

Such a nice place! Walking distance to the beach. The staff are very friendly and responsive. Our room was very clean and modern. Great stay!!

Reviewed on Sep 10, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,088

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (591 reviews)

Everything is Good

Reviewed on Sep 13, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$930

per person

Dec 1 - Dec 6

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

The location was wonderful, the view was beautiful, the hotel was very clean, I loved it. Staff was great.

Reviewed on Sep 14, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,125

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,150 reviews)

Staff was so nice and the beds are amazing!

Reviewed on Sep 14, 2026

Legacy Hotel at IMG Academy

Save 100% on your flight

$1,589

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,003 reviews)

Everything was great.

Reviewed on Sep 12, 2026

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.

A cityscape with a mix of modern and historic buildings, palm trees, and a cloudy sky.

South Sarasota

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

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

Beaches, exotic gardens and a museum for a famous circus are located in the city’s central sector. Visit an upscale shopping area on an island of its own.

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

Downtown Sarasota

If you're spending some time in Downtown Sarasota, Sarasota Opera House and Regal Hollywood - Sarasota are top sights worth seeing.

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

Palmer Ranch

When in Palmer Ranch, you can plan a visit to Stoneybrook Golf & Country Club and Sarasota Square, some noteworthy sights in the nearby area.

Oyster Bay Hotel Deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Fully refundableReserve now, pay when you stay

$62 nightly

$71 total

Sep 21 - Sep 22

Total with taxes and fees

9.2/10 Wonderful! (5,995 reviews)

"Me gusto mucho en general. La atenciónexelente, el desayuno muy bueno. Volvería sin dudas."

Reviewed on Sep 14, 2026

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Fully refundableReserve now, pay when you stay

$169 nightly

$191 total

Sep 27 - Sep 28

Total with taxes and fees

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Fully refundableReserve now, pay when you stay

$150 nightly

$169 total

Sep 15 - Sep 16

Total with taxes and fees

9.4/10 Exceptional! (5,874 reviews)

"Rooms were in beautiful condition property was beautiful also pool and water falls 3 of them already booked for next trip beach was 1 minute walking distance"

Reviewed on Sep 14, 2026

See all 13,549 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.