Keewaydin Island Vacations from $264

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The Latest Keewaydin Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

Save 100% on your flight
$264
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
6.8/10 (1,145 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$822
per person
Oct 10 - Oct 17
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (992 reviews)
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight
$667
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (87 reviews)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight
$558
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,002 reviews)
Casa Ybel Resort

Casa Ybel Resort

Mid Island
Save 100% on your flight
$1,000
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (391 reviews)
I’ve been staying at Casaybel for 49 years! Everything was great! Rooms very clean. The pool was good. The only problem I had was the front desk with a package that was delivered by the post office through Amazon that showed delivered yet the girl said there was no package and she would check the mailbox. The next day no call. So when we came back from dinner I stopped at the mail box and it was packed with mail and my package! I wonder how often they check the mailbox? Also I paid for weekly chairs and umbrella at the beach. One day it rained in the morning. I called and left a message for my chairs after the sun was shining and no call and no chairs. I found people on the beach with chairs and asked if they were brought out for them and she told me she retrieved them herself. No compensation. I understand they have staff issues with the beach stuff but then they shouldn’t offer them when 2 chairs and 1 umbrella cost $150 per week when I could have ordered them from Billy’s. My family owns 6 weeks and we love it! I also rented this week in the 1 bedrooms through Expedia since my family is growing. Maybe they could do better with the problems I experienced. Thanks for listening. Oh and also we saw a coyote walking around between the beach and the building 😳

Reviewed on Aug 9, 2026

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What to do in Keewaydin Island

Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

$66
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

$57
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

$78
per adult
Naples: Sightseeing and Dining Cruises
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Keewaydin Island Hotel Deals

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
$218 nightly
$241 total
Aug 30 - Aug 31
Total with taxes and fees
Hilton Marco Island Beach Resort and Spa
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL
Fully refundableReserve now, pay when you stay
$144 nightly
$160 total
Sep 7 - Sep 8
Total with taxes and fees
Hyatt House Naples/5th Avenue
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL
$161 nightly
$179 total
Aug 11 - Aug 12
Total with taxes and fees
9.4/10 Exceptional! (1,176 reviews)
"Me encanta"

Reviewed on Aug 10, 2026

Great Wolf Lodge Naples
See all 10,580 properties in Keewaydin Island
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.

Find the Best Keewaydin Island Vacation Packages

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January65.7°F (18.7°C)No RainMostly SunnyAverageAverage
February68.2°F (20.1°C)No RainSunnyAverageSlightly High
March70.3°F (21.3°C)No RainSunnySlightly HighSlightly High
April75.4°F (24.1°C)No RainSunnySlightly HighSlightly High
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnySlightly HighAverage
July83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
August84.0°F (28.9°C)Light RainMostly SunnySlightly LowSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnySlightly LowSlightly Low
November73.0°F (22.8°C)No RainMostly SunnySlightly LowAverage
December69.3°F (20.7°C)No RainMostly SunnyAverageAverage

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.

Keewaydin Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Southwest Florida Intl. Airport (RSW)

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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.