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A coastal landscape with a sandy beach, clear turquoise waters, and a network of small islands.

Keewaydin Island Vacations from $534

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The Latest Keewaydin Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • 2 outdoor pools, cabanas (surcharge), pool umbrellas
    Oct 2 - Oct 5

    The Perry Hotel Naples + Flight

    Naples
    3 nights
    4.5 star property
    9.6/10 - Exceptional (965 reviews)
    "We were early and was able to check in. They front desk employee was very pleasant and made sure we had a room with a good view, since we were celebrating a special birthday. We felt special and were very pleased with our experience. "
    Reviewed July 24, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • 1 stop RSW - BOS • 1 stop
    Save 100% on your flight
    $809
    $534
    per traveler
    found 1 day ago
    The Perry Hotel Naples
  • View from room
    Sep 25 - Sep 28

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

    Vanderbilt Beach
    3 nights
    4.5 star property
    9.0/10 - Wonderful (1,002 reviews)
    "Excelent"
    Reviewed July 24, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • 1 stop RSW - BOS • 1 stop
    Save 100% on your flight
    $1,138
    $666
    per traveler
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • Luxury House, Pool View | Pool | Outdoor pool
    Sep 14 - Sep 20

    A Wave From it All + Flight

    Siesta Isle
    6 nights
    2.0 star property
    Roundtrip • Minneapolis (MSP) - Fort Myers (RSW)
    MSP - RSW • Nonstop RSW - MSP • Nonstop
    Save 100% on your flight
    $2,664
    $1,721
    per traveler
    found 14 hours ago
    A Wave From it All
  • Aerial view
    Sep 10 - Sep 15

    Tween Waters Island Resort & Spa + Flight

    Captiva
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,002 reviews)
    "The balcony looks right at ocean making for beautiful view."
    Reviewed July 24, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • 1 stop RSW - BOS • Nonstop
    Save 100% on your flight
    $1,205
    $809
    per traveler
    found 1 day ago
    Tween Waters Island Resort & Spa
  • Private beach, surfing, kayaking, rowing
    Sep 26 - Sep 30

    Manasota Key Resort + Flight

    Manasota Key
    4 nights
    2.5 star property
    9.4/10 - Exceptional (304 reviews)
    "We were only on property for 10 minutes before agreeing that we needed to come back every year. It is a little piece of paradise. We used all the things, from lawn chairs to shuffle boards, paddle boards, bikes, and pool. It is a short drive to restaurants and stores, but the kitchenette was perfect for cooking a quick meal. The rooms are spacious and comfortable."
    Reviewed July 16, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop RSW - BOS • Nonstop
    Save 100% on your flight
    $1,273
    $860
    per traveler
    found 1 day ago
    Manasota Key Resort

Keewaydin Island Hotel Deals

Terrace/patio

Hampton Inn & Suites Naples South

Hampton Inn & Suites Naples South
2.5 star property
3.4 mi from Keewaydin Island
9.8 out of 10, Exceptional, (541 reviews)
"Excelent choice"
$93 nightly
The price is $104
Aug 9 - Aug 10
Total with taxes and fees
Hampton Inn & Suites Naples South
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.
See all properties in Keewaydin Island

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Things to do near Keewaydin Island

Keewaydin Island offers a perfect escape for beach lovers and adventure seekers alike. Visitors can enjoy a variety of activities such as beach excursions, wildlife tours, and the exciting Keewaydin Tiki Boat Island Adventure. With its beautiful recreational areas and centers, the island is ideal for day trips and relaxing beach vacations, ensuring a memorable outdoor experience for everyone.

Shopping

For a great shopping experience near Keewaydin Island, visit Tin City, just 5 miles away, offering entertainment and family vibes. The Naples Outlet Center, 6 miles away, features various shops and dining. Lastly, explore Village on Venetian Bay, 9 miles away, known for its charming atmosphere and unique finds.

Recreation

Relax at East Naples Community Park, where you can enjoy serene walking trails and tranquil picnic areas. For sports enthusiasts, TPC Treviso Bay offers a stunning golf experience surrounded by nature. Alternatively, indulge in luxury at Mustang Course - Lely Resort, a private club perfect for unwinding in style.

Adventure

Experience the thrill of the ocean at Sanibel Sea School, located 30 miles from Keewaydin Island, where you can explore underwater sports. For family fun, visit Beach Bowl, also 30 miles away, featuring arcade adventures. Don’t miss Marco Island Ski & Watersports, just 10 miles away, offering exciting water sports.

Nightlife

Keewaydin Island offers a laid-back nightlife with beach bonfires and sunset views. Enjoy cocktails at local beach bars, or join a sunset cruise for stunning vistas. For a relaxed vibe, gather around fire pits under the stars and soak in the island's tranquil charm.

Find the best attractions near Keewaydin Island

Keewaydin Island, Florida, is a paradise for beach lovers and outdoor adventurers. This idyllic destination offers pristine beaches, scenic marinas, and vibrant local culture. Visitors can explore various attractions, enjoy island vacation packages, and take in the diverse wildlife. Whether you're seeking relaxation or adventure, Keewaydin Island provides an unforgettable experience with its beautiful amenities and outdoor activities, making it a perfect spot for your next getaway.

  • Naples Beach: Located 4 miles from Keewaydin Island, Naples Beach offers a pristine stretch of white sand and warm Gulf waters. The beach vibe is perfect for relaxation, sunbathing, and enjoying water activities like swimming and paddleboarding. The stunning sunsets here are a must-see.
  • Fifth Avenue South: About 5 miles away, Fifth Avenue South is the heart of Naples’ city life, lined with upscale shops, art galleries, and gourmet restaurants. This vibrant street atmosphere is perfect for strolling, dining, and indulging in local culture.
  • Naples Pier: Situated 4 miles from Keewaydin Island, Naples Pier is ideal for fishing, dolphin watching, or simply enjoying the scenic views. The pier's excursions vibe invites visitors to take leisurely walks and soak in the ocean breeze.

Best time to go to Keewaydin Island

The best time to visit Keewaydin Island, Naples is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

Tips to save on your trip to Keewaydin Island

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically August to October) for more affordable package holidays to Keewaydin Island.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.