Oyster Bay Vacation Packages

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Top Holiday Package Deals in Oyster Bay

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

Landing Apartments Fort Myers near Olympia Pointe

CA $994

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

8.8/10 Excellent! (9 reviews)

Great pool,comfortable room.

Reviewed on Mar 27, 2026

Landing Furnished Apartments minutes from Downtown Fort Myers

Hancock

CA $1,295

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

No reviews

Matanzas Inn Bayside Resort and Marina

CA $1,058

per person

Nov 27 - Dec 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Fort Myers (RSW)

9.4/10 Exceptional! (1,006 reviews)

We stayed one night but will definitely be back for a longer stay. Everyone was helpful and friendly. I loved that there was free parking and an ice machine! Our room was clean and roomy.

Reviewed on Sep 14, 2026

The Lighthouse Resort Inn & Suites

CA $1,007

per person

Nov 27 - Dec 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Fort Myers (RSW)

8.6/10 Excellent! (1,787 reviews)

Very close to the Beach. Pool is nice and bar is outstanding

Reviewed on Sep 13, 2026

Landing Apartments Fort Myers near Eastwood Village

CA $1,072

per person

Nov 27 - Dec 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Fort Myers (RSW)

9.6/10 Exceptional! (30 reviews)

This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 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 person carrying a child on their shoulders on a bridge with a view of greenery and a clear sky.

Central Naples

1 out of top 10 points of interest in this area

If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing.

A pink and white orchid plant with a rocky background.

East Naples

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.

A pier extending into a calm sea at sunset with a beach on the right.

Old Naples

3 out of top 10 points of interest in this area

The stunning beaches and popular shops are just a few highlights of Old Naples. Make a stop by Fifth Avenue South or Naples Beach while you're exploring the area.

A coastal landscape with a cruise ship, dense greenery, and a clear view of the ocean.

Naples Park

Located in North Naples, Naples Park is bounded by U.S. Route 41 and offers easy access to Vanderbilt Lagoon. Enjoy shopping at the nearby outdoor mall, The Mercato, for a delightful experience.

A sailboat with a blue canopy on calm waters, a red buoy, and a forested shoreline.

Vanderbilt Beach

1 out of top 10 points of interest in this area

While visiting Vanderbilt Beach, you might make a stop by sights like Vanderbilt Beach and Delnor-Wiggins Pass State Park.

Oyster Bay Hotel Deals

Naples Bay Resort & Marina

1500 Fifth Ave S Naples FL

Fully refundableReserve now, pay when you stay

CA $256

per night

Sep 21 - Sep 22

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL

Fully refundableReserve now, pay when you stay

CA $263

per night

Oct 6 - Oct 7

9/10 Wonderful! (2,042 reviews)

"El hotel muy bueno todo! Pero el restaurante super caro, un menu muy reducido y ordenamos un ceviche de camarones y habían 4 camarones picado por la mitad y se vegan 8 pedazos muy mal se ve esto."

Reviewed on Sep 17, 2026

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL

Fully refundableReserve now, pay when you stay

CA $101

per night

Oct 4 - Oct 5

See all 11,003 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.