Oyster Bay Vacations from $723
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The Latest Oyster Bay Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $1,305, price is now $723 per person
$723
per person
Feb 27 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Staff was fantastic. Room was nice and overall great experience.
Reviewed on Dec 7, 2025
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $2,582, price is now $1,443 per person
$1,443
per person
Feb 27 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Room was amazing! View spectacular! Service the best!
Reviewed on Dec 7, 2025
Innovation Hotel
Save 100% on your flight
Price was $1,557, price is now $945 per person
$945
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
Nice, spacious rooms. Good bar and restaurant. Great gym. Also, no children!
Reviewed on Dec 4, 2025
South Seas Resort
Save 100% on your flight
Price was $1,807, price is now $1,113 per person
$1,113
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,001 reviews)
We stayed several days at a bayside building 1 BR unit not far from reception. Everything was new and it was well fit out for using the kitchen and generally well supplied in the baths. There were two full bathrooms and full sized applicances. A full sized mirror was one missing thing. The resort is still recovering from the hurricanes but is close to looking normal. When we were there they were activating the water park and working on landscaping around our building and pool. The village of Captiva is in walking distance. We walked in because parking is VERY limited, although paid parking is at the Marina. The general store and resaturants in town were pricey but fine. They are adding a berm dune to the beaches, so there was still construction there and the beached look stark, but they are fully useable where open.
Reviewed on Nov 24, 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
$422 nightly
The price is $463 total per night from Dec 9 to Dec 10
$463 total
Dec 9 - Dec 10
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
With the airport near by and the marina, a lot of noise pollution
Reviewed on Nov 29, 2025
Naples Grande Beach Resort
475 Seagate Drive Naples FL
Fully refundable
$401 nightly
The price is $446 total per night from Dec 21 to Dec 22
$446 total
Dec 21 - Dec 22
Total with taxes and fees
9/10 Wonderful! (1,962 reviews)
Great location
Reviewed on Dec 7, 2025
Inn on Fifth
699 5th Ave S Naples FL
Fully refundable
$315 nightly
The price is $350 total per night from Dec 16 to Dec 17
$350 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
The room was clean and bright when we walked in. Lights were turned on and the bathroom was very spacious. The front desk staff was very courteous. I would definitely come back to stay while visiting Naples.
Reviewed on Dec 5, 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
4.5/5(1,407 reviews)
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.
Vanderbilt Beach
4.5/5(313 reviews)
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.
Fifth Avenue South
4.5/5(45 reviews)
Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.
Things to do
Sunset Tour in Naples Bay on a New Godfrey- All included
$110
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.