Three Oaks Vacations from $468
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Three Oaks Vacation
Choose a Three Oaks vacation package and focus on what matters — enjoying yourself. There's no more planning nightmares, just more time to savor the charms of this interesting city, such as its artistic creativity and rich history. JetBlue Park at Fenway South, Hertz Arena and Florida Gulf Coast University are just some of the attractions worth visiting during your trip to Three Oaks. That dream Three Oaks vacation is a couple of clicks away. Browse airfares, hotels and more on Expedia for an adventure that's tailored to suit your style.
The Latest Three Oaks Vacation Packages
Price found within the past 48 hours. Click for updated prices.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,688, price is now $945 per person
$945
per person
Aug 12 - Aug 17
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,009 reviews)
It was amazing and the room was spectacular
Reviewed on Jul 4, 2026
Inn on Fifth
Old Naples
Save 100% on your flight
Price was $1,387, price is now $848 per person
$848
per person
Aug 12 - Aug 17
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,005 reviews)
Clean, great customer service, and located on the Main Street with restaurants and shops.
Reviewed on Jul 1, 2026
Harbour House At The Inn
Save 100% on your flight
Price was $1,270, price is now $832 per person
$832
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
9.2/10 Wonderful! (773 reviews)
This property is awesome! We have stayed here several times and have had exceptional customer service, excellent location and the property is clean and very well maintained. Convenient parking is a plus too!
Reviewed on Jun 29, 2026
Where to stay in Three Oaks
Find the best Three Oaks areas and neighborhoods for the activities you enjoy most. Learn more about Three Oaks
Iona
While visiting Iona, you might make a stop by sights like Estero Bay Preserve State Park and Tribby Arts Center.
Three Oaks Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$255 nightly
The price is $284 total per night from Jul 6 to Jul 7
$284 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (2,289 reviews)
"The drinks at the fins up pool/bar sucked."
Reviewed on Jul 3, 2026
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $153 total per night from Jul 8 to Jul 9
$153 total
Jul 8 - Jul 9
Total with taxes and fees
9/10 Wonderful! (1,696 reviews)
"It was the worst stay, the bed was not good, everything was just extremely uncomfortable and not clean. Had to sleep on the floor…"
Reviewed on Jul 3, 2026
Sanibel Island Beach Resort
1231 Middle Gulf Dr Sanibel FL
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $280 total per night from Aug 2 to Aug 3
$280 total
Aug 2 - Aug 3
Total with taxes and fees
9.2/10 Wonderful! (2,086 reviews)
"The room is very clean and updated. Staffs were friendly and prompt when asked for something extra for the room. Appreciate the text messages that we can communicate with staffs on the go."
Reviewed on Jul 4, 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.
Things to do
Fort Myers Beach Sunset and Dolphin Watching Cruise
$59
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.