Three Oaks Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.

Top Holiday Package Deals in Three Oaks

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,244, price is now CA $920 per person
CA $920
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (851 reviews)
Excellent stay, beautiful property with friendly staff. Shout out to Regina for top notch customer service at check -in and check out! Yvette who made delicious cocktails with our rooftop lunch and later sunset drinks at the Tigress was fantastic too. Pool was immaculate and relaxing, lush chair covers and floating beds. Minutes from Vanderbilt beach and shopping areas. We will be back!

Reviewed on Jun 15, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $1,812, price is now CA $1,230 per person
CA $1,230
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,012 reviews)
Property was beautiful, well maintained. Staff was beyond phenomenal and spa service was amazing!

Reviewed on Jun 14, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was CA $1,781, price is now CA $1,211 per person
CA $1,211
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.8/10 Exceptional! (1,228 reviews)
Exceeded our expectations. Everything that we needed was there in one place, including boat rentals, restaurants, bars, shopping, and great water views.

Reviewed on Jun 12, 2026

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Price was CA $1,401, price is now CA $1,019 per person
CA $1,019
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (357 reviews)
Excellent place, great location, the ocen is just steps from the condo, nice pool for swim laps! will definitely return, thank you for having us.

Reviewed on Jun 11, 2026

Latitude 26 Waterfront Resort & Marina

Latitude 26 Waterfront Resort & Marina

3 out of 5
Price was CA $1,536, price is now CA $1,149 per person
CA $1,149
per person
Aug 8 - Aug 15
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
Great room. Very clean but there was an old smell of cigarette in the room. Other than that it was a great stay!

Reviewed on Jun 14, 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
Aerial view of the road bridge between Captiva Island and Sanibel Island in Lee County, Florida, United States

Iona

While visiting Iona, you might make a stop by sights like Estero Bay Preserve State Park and Tribby Arts Center.

Find hotels in Iona

Three Oaks Hotel Deals

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Jun 29 to Jun 30
CA $267
CA $347 total
Jun 29 - Jun 30
includes taxes & fees
8.6/10 Excellent! (1,023 reviews)
"Great location to access the island. I always book here for visitors so they can access SanCap and FMB and Fort Myers easily."

Reviewed on Jun 15, 2026

Marriott Sanibel Harbour Resort & Spa
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is CA $257 per night from Jun 16 to Jun 17
CA $257
CA $356 total
Jun 16 - Jun 17
includes taxes & fees
9/10 Wonderful! (2,209 reviews)
"El hotel muy limpio , buena atención , buen trato pero si debo señalar que en la playa las embarcaciones y los botes particulares (fuera de los huéspedes) no dan espacio para los q pagan un servicio hotelero , vienen prácticamente a la orilla y los que han pagado apenas cuentan con tranquilidad para ..."

Reviewed on Jun 15, 2026

Margaritaville Beach Resort Fort Myers
Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

2.5 out of 5
4850 S Cleveland Ave Fort Myers FL
Fully refundableReserve now, pay when you stay
The price is CA $91 per night from Jun 19 to Jun 20
CA $91
CA $101 total
Jun 19 - Jun 20
includes taxes & fees
6.8/10 (1,135 reviews)
"The Bruun Smells nasty. The beds are uncomfortable. The towels are old."

Reviewed on Jun 14, 2026

Baymont by Wyndham Fort Myers Central
See all 17,704 properties in Three Oaks
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.
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Frequently asked questions

How much does a Three Oaks vacation package cost?
Live it up in Three Oaks from as little as CA $920. We offer a great selection of flights, rental cars and hotels to suit every budget. You can score even better deals when you add a few activities or tours to your package.
How do I get a cheap travel package to Three Oaks?
If you love amazing deals, combine your bookings into a Three Oaks vacation package. Whether you're chasing hotels, flights, rental cars or day tours, you can book everything in one place. You'll have lots of choice at your fingertips too. Expedia has over 550 partner airlines and 1,000,000 hotels around the world to take your pick of. Fly with who you want, stay where you like and save precious money — now that's the perfect escape!
Where should I stay in Three Oaks?
Make sightseeing easy by staying in a hotel just around the corner from Three Oaks's main attractions. Edison and Ford Winter Estates and Manatee Park are two of the best in the area.
How far in advance should I book my Three Oaks vacation?
It depends on the air carrier, but you can usually look up international fares on Expedia up to a year in advance. While it's generally recommended to book ahead of time, lucky customers will sometimes find a cheaper flight just weeks prior to departure dates.
What does an Expedia Three Oaks travel package include?
That depends entirely on you. You can select from a range of Three Oaks bundles, such as a rental car, flight and hotel. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your dream Three Oaks break looks like, you're sure to save!
What should I know before booking a Three Oaks travel package?
Our prices are always low. However, you'll score even better deals if you book your flights, hotels and car rentals together. With an Expedia travel package, you'll get transparent pricing and a huge range of choice.
Can I choose my airline with a Three Oaks Expedia vacation package?
Most definitely. We offer more than 550 partner airlines around the world, so you can tailor your Three Oaks escape according to your budget and style.
If I'm not able to travel, can I cancel my Three Oaks vacation package?
Don't worry if you're rethinking your Three Oaks vacation package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We totally understand life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.