Three Oaks Vacations from $628

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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.

The Latest Three Oaks Vacation Packages

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

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,014, price is now $628 per person
$628
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (725 reviews)
Kev and bellmen Jon gave my family and I so much kindness and compassion during my stay and I will be forever grateful to them and all the staff at this property

Reviewed on Apr 11, 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 $2,589, price is now $1,268 per person
$1,268
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,002 reviews)
Location right on beach is what you are paying for- the beach is beautiful and steps from the hotel. Staff is great and very friendly. Rooms are average and need maintenance. The light over the shower had water coming through it (scary) and the door to the room whistled when the wind blew. Food choices are limited and way over priced for the quality. Dinner at Balene was disappointing - my lobster was chewy. No other eating establishments are close enough to walk to so you have to either drive or order food if you don't want to eat onsite the entire time. Overall we had a nice time because we came for beach and sun, but would not stay here again.

Reviewed on Apr 11, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $1,219, price is now $790 per person
$790
per person
Jun 14 - Jun 19
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (821 reviews)
Small selection of food options on site. Bar was understaffed. Pool and lazy river were wonderful.

Reviewed on Apr 9, 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,030, price is now $689 per person
$689
per person
Jun 23 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,008 reviews)
So close to everything! The beach and restaurants were only a block away. The rooms were spacious and the pool area was great. Nice and quiet location as well. We will be back!

Reviewed on Apr 11, 2026

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,209, price is now $809 per person
$809
per person
Jun 23 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,702 reviews)
View was excellent, room was clean. Unfortunately construction right next to property started the week we were there. Also I think that if you book through a third party like Expedia you get the less desirable room—-we ended up having to book an extra day bc our flight as delayed by 12 hours and so it was very obvious that the room we moved to was much much better—more updated—than the one we stayed in for the first four days. Not a big fan of Ft Myers—had zero good meals. The location of our place was great though—away from all of the noise/busyness but close enough to walk.

Reviewed on Apr 11, 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

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

2.5 out of 5
1538 Cape Coral Pkwy E Cape Coral FL
Fully refundable
$101 nightly
The price is $113 total per night from May 11 to May 12
$113 total
May 11 - May 12
Total with taxes and fees
9.2/10 Wonderful! (1,386 reviews)
Room was neat, clean and tidy. Staff was friendly, breakfast was good and filling. Able to park easily.

Reviewed on Apr 11, 2026

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
$293 nightly
The price is $327 total per night from May 13 to May 14
$327 total
May 13 - May 14
Total with taxes and fees
9/10 Wonderful! (2,006 reviews)
Awesome

Reviewed on Apr 11, 2026

Margaritaville Beach Resort Fort Myers
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr Sanibel FL
Fully refundableReserve now, pay when you stay
$264 nightly
The price is $292 total per night from May 7 to May 8
$292 total
May 7 - May 8
Total with taxes and fees
9.2/10 Wonderful! (1,769 reviews)
Great place to vacation! The beach was so close we could just stroll to it everyday. The staff was very amenable and prompt. The property is slightly old but rooms were clean and quiet. We got our best sleep in a long time! Thanks folks!

Reviewed on Apr 10, 2026

Sanibel Island Beach Resort
See all 17,581 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Three Oaks

Edison Mall

Edison Mall

You can enjoy retail therapy at Edison Mall during your visit to Fort Myers. Attend a baseball game or discover the beautiful sunsets in this family-friendly area.

Edison Mall
Edison and Ford Winter Estates

Edison and Ford Winter Estates

Explore the winter estates of two of the most famous men in American history. Tour their houses and gardens and learn more about their lives in the museum.

Edison and Ford Winter Estates
Sanibel Harbour

Sanibel Harbour

Commune with nature and explore the great outdoors at Sanibel Harbour during your travels in Fort Myers. Stroll along the waterfront or visit the spas in this family-friendly area.

Sanibel Harbour

Things to do

Fort Myers Beach Sunset and Dolphin Watching Cruise

Fort Myers Beach Sunset and Dolphin Watching Cruise

$70
per adult
100% of travellers recommend
Fort Myers Beach Sunset and Dolphin Watching Cruise
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

$70
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Copacetic Day Sail

Copacetic Day Sail

$70
per adult
100% of travellers recommend
Copacetic Day Sail
See all activities in Fort Myers
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.