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.
The Lighthouse Resort Inn & Suites
Price was CA $1,731, price is now CA $1,137 per person
CA $1,137
per person
Jul 10 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,630 reviews)
Our room was right on top of Tiki Hut where every night music was so loud couldn’t sleep. When I asked to be moved front desk told me Expedia should have warned me that the room would be noisy and nothing available…. Otherwise place had nice pool , breakfast good in morning and two block walk to beach.
Reviewed on May 5, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was CA $3,032, price is now CA $1,708 per person
CA $1,708
per person
Jul 25 - Aug 1
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9/10 Wonderful! (1,001 reviews)
Nice, high end facility with friendly staff. Check in was easy, check out was easy, going to the beach was easy… very relaxing stay.
Reviewed on May 4, 2026
The Perry Hotel Naples
Price was CA $1,832, price is now CA $1,164 per person
CA $1,164
per person
Jun 8 - Jun 15
found 10 hours ago
Roundtrip flight included
Montreal (YMQ) to Fort Myers (RSW)
9.4/10 Exceptional! (776 reviews)
Everything was terrific from the beautiful rooms, 2 pools, excellent and helpful staff to the breakfast bar in the morning. There are shuttles by van and boat to the beaches abs other locations. The new Tigress restaurant and outdoor bar were a perfect way to end the day.
Reviewed on May 3, 2026
Mariners Boathouse by Coolvacay
South Island
Price was CA $1,907, price is now CA $1,260 per person
CA $1,260
per person
Jul 10 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
10/10 Exceptional! (1 review)
Hurricane Ian decimated the area but the residents are working hard to bring it back to its glory days. This resort has undergone an amazing renovation and they are doing more and more every day. Their new pool and Jacuzzi is stunning. The location is perfect. The staff is wonderful!
Reviewed on Apr 29, 2026
Casa Playa Beach Resort
Price was CA $2,037, price is now CA $1,377 per person
CA $1,377
per person
Jul 10 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (195 reviews)
right on the beach. Very quiet and peaceful . Not crowded. Comfortable and clean room with balcony and spectacular view of the ocean
Reviewed on Apr 25, 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
East Naples
4/5(11 area reviews)
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.
Oyster Bay Hotel Deals
Naples Bay Resort & Marina
1500 Fifth Ave S Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $306 per night from May 10 to May 11
CA $306
CA $339 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (1,023 reviews)
Great place
Reviewed on May 7, 2026
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
The price is CA $324 per night from May 25 to May 26
CA $324
CA $435 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (1,773 reviews)
Beautiful property with fantastic beach.
Reviewed on May 6, 2026
Great Wolf Lodge Naples
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $353 per night from May 10 to May 11
CA $353
CA $392 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (771 reviews)
Muy linda la extacion
Reviewed on May 6, 2026
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.
Discover the most popular places to visit in Oyster Bay
Naples Beach
Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.
Fifth Avenue South
Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.
Vanderbilt Beach
If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.
Things to do
Naples Florida: Downtown Electric Trike Tour - Family Fun
CA $68
per adult
100% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
CA $101
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.