Oyster Bay Vacations from $483
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The Latest Oyster Bay Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $775, price is now $483 per person
$483
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (639 reviews)
Had a great time, the pools and lazy river were more than welcome on the hot days. The water shuttle to the private beach is a great feature, just be sure to signup in advance. Having our own vehicle gave us the chance to explore more of the areas activities and restaurants. The Only downsides were communication with having our room being cleaned or fresh towels, and the pesky room keys that would randomly stop working. Would visit again and had a great time.
Reviewed on Oct 2, 2025
The Perry Hotel Naples
Save 100% on your flight
Price was $2,549, price is now $1,661 per person
$1,661
per person
Dec 26 - Dec 30
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (417 reviews)
Great all around 10/10 ; tigress restaurant is worth checking out as well
Reviewed on Sep 28, 2025
Bellasera Resort
Old Naples
Save 100% on your flight
Price was $3,054, price is now $2,013 per person
$2,013
per person
Dec 19 - Dec 25
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,219 reviews)
Joyful, relax and exceptional place in the center of the town. People at reception thanks to Tesse and her coworker was pleasant and welcoming , menu at Claw Bar and the London Club superbly delicious , service above and beyond accommodating , dream team of the cleaning crew (spotless clean, but invisible) , valet people friendly and entertaining . Whole experience during our stay was just perfect . Thank you , Bellasera , we will be back
Reviewed on Sep 29, 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
East Naples
4/5(171 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
$204 nightly
The price is $221 total per night from Oct 6 to Oct 7
$221 total
Oct 6 - Oct 7
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"Property was beautiful"
Reviewed on Sep 29, 2025
Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
$235 nightly
The price is $261 total per night from Oct 14 to Oct 15
$261 total
Oct 14 - Oct 15
Total with taxes and fees
9/10 Wonderful! (1,825 reviews)
"Wonderful staff and fast elevators!! Clean facilities and room service was phenomenal"
Reviewed on Sep 30, 2025
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd, Marco Island, FL
Fully refundableReserve now, pay when you stay
$243 nightly
The price is $270 total per night from Oct 13 to Oct 14
$270 total
Oct 13 - Oct 14
Total with taxes and fees
8.8/10 Excellent! (1,592 reviews)
"The beach is beautiful and the staff will set you up with lounge chairs and an umbrella. The short walk to the beach is enjoyable with lush tropical plants along the walkway and then opening up to a beautiful gulf beach. The pool and spa area are very nice with the wonderful staff serving food and ..."
Reviewed on Oct 4, 2025
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
Naples Florida: Downtown Electric Trike Tour - Family Fun
$56
per adult
100% of travellers recommend
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour
$127
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.