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

Three Oaks Vacations from $351

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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 hotel room with a large bed, bedside tables, a desk, and a window with curtains.
    Jan 20 - Jan 24

    Quality Inn Fort Myers Cape Coral + Flight

    Fort Myers
    4 nights
    2.0 star property
    7.6/10 - Good (515 reviews)
    "Got my booking wrong, took 1 hour and a half to even get them to offer a different room that could meet my accommodation. Not to mention the manager never contacted me for anything. Do not book here"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - RSW • Nonstop RSW - PSM • 1 stop
    $520
    $351
    per traveler
    found 1 day ago
    Quality Inn Fort Myers Cape Coral
  • A balcony with a view of the beach, white railings, and a lounge chair with towels.
    Dec 13 - Dec 19

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

    Vanderbilt Beach
    6 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
    $2,244
    $1,308
    per traveler
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • A balcony with a view of a beach, a table, and chairs.
    Dec 17 - Dec 22

    Windward Passage Resort + Flight

    Fort Myers Beach
    5 nights
    2.0 star property
    8.6/10 - Excellent (23 reviews)
    "Location is amazing, being right on the beach. Having access to beach chairs to take down to the beach and return is a major plus. Gas grills on the property also give you the opportunity to grill up some dinner and watch the sunset while eating on your balcony!! I would definitely recommend!"
    Reviewed October 31, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $1,152
    $741
    per traveler
    found 1 day ago
    Windward Passage Resort
  • A large swimming pool surrounded by lounge chairs and palm trees, with a hotel building in the background.
    Jan 14 - Jan 18

    Sunsuites Villas At Sunseeker Resort, Curio By Hilton + Flight

    Charlotte Harbor
    4 nights
    4.0 star property
    9.4/10 - Exceptional (147 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - MCO • 1 stop MCO - BOS • 1 stop
    $1,088
    $705
    per traveler
    found 1 day ago
    Sunsuites Villas At Sunseeker Resort, Curio By Hilton
  • A resort with a central pool, multiple lounge areas, and a beach view.
    Jan 20 - Jan 24

    Tween Waters Island Resort & Spa + Flight

    Captiva
    4 nights
    3.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "This is a great property,"
    Reviewed November 2, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - RSW • Nonstop RSW - PSM • 1 stop
    $1,012
    $665
    per traveler
    found 1 day ago
    Tween Waters Island Resort & Spa

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

An outdoor seating area with a fire pit, outdoor furniture, and a covered patio.

TownePlace Suites by Marriott Fort Myers Gulf Coast

TownePlace Suites by Marriott Fort Myers Gulf Coast
3.0 star property
1.7 mi from Three Oaks
9.2 out of 10, Wonderful, (284 reviews)
$95 nightly
The price is $106
Nov 28 - Nov 29
Total with taxes and fees
TownePlace Suites by Marriott Fort Myers Gulf Coast
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.