Oyster Bay Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 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
Top Holiday Package Deals in Oyster Bay
Price found within the past 48 hours. Click for updated prices.
Innovation Hotel
Price was CA $1,257, price is now CA $749 per person
CA $749
per person
Oct 22 - Oct 26
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.8/10 Exceptional! (512 reviews)
Everything was amazing except for the fan in the room continually blowing and making noise.
Reviewed on Aug. 20, 2025
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was CA $4,337, price is now CA $1,908 per person
CA $1,908
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.8/10 Excellent! (1,004 reviews)
Ants in room-service was just okay-place needs updating-prices very high for what you get. Lack of attention to detail-Balleen was just fair-signature grouper dish highly recommended by server was warm (not hot) and risotto cake was undercooked (and for $65 per portion ????? ) overall price for value received was WAY TO HIGH).
Reviewed on Aug. 29, 2025
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was CA $1,448, price is now CA $877 per person
CA $877
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.2/10 Wonderful! (606 reviews)
Great hotel with amazing pools and lazy river. They also have a free private island with boat transportation. Overall loved the experience.
Reviewed on Aug. 30, 2025
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
Old Naples
3 out of top 10 points of interest in this area
5/5(25 area reviews)
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.
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 $344 per night from Sep 1 to Sep 2
CA $344
CA $454 total
Sep 1 - Sep 2
includes taxes & fees
Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
Fully refundable
The price is CA $216 per night from Sep 7 to Sep 8
CA $216
CA $309 total
Sep 7 - Sep 8
includes taxes & fees
Hyatt House Naples/5th Avenue
1345 5th Avenue South, Naples, FL
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Sep 5 to Sep 6
CA $175
CA $194 total
Sep 5 - Sep 6
includes taxes & fees
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.
Naples Pier
Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.
Things to do
Manatee Sightseeing and Wildlife Boat Tour
CA $96
per adult
90% of travellers recommend
Naples Florida: Downtown Electric Moped Tour
CA $96
per adult
100% of travellers recommend
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.