A pier extending into the ocean with two lookout towers, waves crashing at the shore, and a sunset sky.

Three Oaks Vacations from $690

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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.
  • A modern building entrance with glass doors, a dark exterior, and potted plants on the sides.
    Jan 21 - Jan 25

    Wiggins Pass Chalet + Flight

    Naples
    4 nights
    4.0 star property
    9.6/10 - Exceptional (301 reviews)
    "Staff were super helpful."
    Reviewed November 9, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $984
    $690
    per traveler
    found 17 hours ago
    Wiggins Pass Chalet
  • A pool area with lounge chairs and umbrellas, surrounded by palm trees.
    Jan 21 - Jan 25

    The Perry Hotel Naples + Flight

    Naples
    4 nights
    4.5 star property
    9.6/10 - Exceptional (1,256 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $1,958
    $1,261
    per traveler
    found 17 hours ago
    The Perry Hotel Naples
  • A balcony with a view of the beach, white railings, and a lounge chair with towels.
    Jan 21 - Jan 25

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,001 reviews)
    "Overall, worth the stay. The place could use some updates."
    Reviewed November 5, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $3,486
    $2,320
    per traveler
    found 17 hours ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.
    Dec 23 - Dec 29

    Bellasera Resort + Flight

    Old Naples
    6 nights
    4.0 star property
    9.6/10 - Exceptional (2,345 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $3,286
    $2,206
    per traveler
    found 1 day ago
    Bellasera Resort
  • A modern kitchen with white cabinetry, a built-in microwave, and a coffee maker. There is a dining area with a round table and chairs.
    Jan 14 - Jan 18

    Spacious Family Retreat Port Charlotte + Flight

    Port Charlotte
    4 nights
    2.0 star property
    10/10 - Exceptional (4 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop RSW - BOS • 1 stop
    $2,651
    $1,820
    per traveler
    found 1 day ago
    Spacious Family Retreat Port Charlotte

Where to stay in Three Oaks

Find the best Three Oaks areas and neighborhoods for the activities you enjoy most.
An aerial view of a coastal area with a bridge connecting two land masses, a beach, and a clear blue sky.

Iona

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

A beach at sunset with the sun reflecting on the water, palm trees, and a clear sky.

Villas

The beaches and abundant dining options are top of the list for many visitors to Villas. A stop by Bell Tower Shops or Regal Belltower might round out your trip.

A bridge over water with a clear sky.

Punta Rassa

Punta Rassa is a destination visitors seek out for is beaches, abundant dining options, and waterfront views. You might want to check out attractions like Sanibel Harbour or Sanibel Harbour Beach while you're exploring the neighborhood.

A pier extending into the water with two gazebos at the end, under a sunset sky.

South Fort Myers

While visiting South Fort Myers, you might make a stop by sights like Estero Bay Preserve State Park and Castle Golf.

Two white birds on a tree branch over water.
Photo by Anthony Ball
Open Photo by Anthony Ball

Daniels Corridor

While visiting Daniels Corridor, you might make a stop by sights like Six Mile Cypress Slough Preserve and Lee Health Sports Complex.

Three Oaks Hotel Deals

A Drury Inn & Suites hotel with a parking lot full of cars.

Drury Inn & Suites Fort Myers Airport FGCU

Drury Inn & Suites Fort Myers Airport FGCU
4.0 star property
Miromar Lakes, 1.5 mi from Three Oaks
9.6 out of 10, Exceptional, (1,005 reviews)
$119 nightly
The price is $133
Dec 1 - Dec 2
Total with taxes and fees
Drury Inn & Suites Fort Myers Airport FGCU
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.