Keewaydin Island Vacation Packages

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Top Keewaydin Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Casa Ybel Resort

Casa Ybel Resort

Mid Island
CA $824
per person
Sep 14 - Sep 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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

South Seas

South Seas

CA $1,547
per person
Oct 31 - Nov 7
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.4/10 Very good! (1,004 reviews)
Beautiful property with excellent amenities—we really enjoyed our stay. One suggestion would be to provide daily housekeeping instead of every other day. Also, while construction is ongoing, it would be appreciated if guests could be assigned rooms farther away from the construction area whenever possible. Unfortunately, our room was very close to it, which made the stay less enjoyable. Overall, it’s a beautiful place, and we would definitely consider staying again.

Reviewed on Aug 2, 2026

The Perry Hotel Naples

The Perry Hotel Naples

CA $1,283
per person
Oct 11 - Oct 17
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
9.6/10 Exceptional! (992 reviews)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

CA $1,705
per person
Nov 1 - Nov 8
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

CA $1,072
per person
Oct 31 - Nov 7
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,002 reviews)

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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
CA $234
CA $337 total
Aug 30 - Aug 31
includes taxes & 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
CA $201
CA $223 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (2,005 reviews)
"The only complaint is about the breakfast: not healthy food meaning the quality of food. Also the capacity of breakfast area and the supply are not according with the demand on Sunday. In another words, please, provide healthier food, it makes the difference."

Reviewed on Aug 10, 2026

Hyatt House Naples/5th Avenue
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL
CA $232
CA $258 total
Aug 11 - Aug 12
includes taxes & 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.

What to do in Keewaydin Island

Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $93
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

CA $80
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

CA $110
per adult
Naples: Sightseeing and Dining Cruises
See all activities in Keewaydin Island

Frequently asked questions

How much does a Keewaydin Island vacation package cost?
Browse and book everything in one place with our Keewaydin Island vacation packages, which start from only CA $824. Select the hotels and flights that suit your style. Then, add on a few experiences or tours for an amazing adventure.
How do I get a cheap travel package to Keewaydin Island?
You'll save big if you bundle your car rentals, hotels and flights into a Keewaydin Island vacation package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer more than 550 airlines and 1,000,000 properties across the world, so you'll always have plenty of options to choose from. Eager to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
Where should I stay in Keewaydin Island?
With popular attractions such as Naples Botanical Garden and East Naples Community Park in this neighborhood, look for a hotel situated near them. Southpointe Marina is another sight in Keewaydin Island that travelers flock to.
How far in advance should I book my Keewaydin Island vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Many air carriers advertise prices up to a year in advance. Usually, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Keewaydin Island sometimes occur just a few weeks before departure.
What does an Expedia Keewaydin Island travel package include?
Travel packages include flights, hotels and rental cars, but you can combine any of them to create your dream Keewaydin Island trip. You can also add on a few tours and activities once you've made your booking. You're the boss! When you combine your bookings with Expedia, you'll enjoy discounts you won't find anywhere else.
What should I know before booking a Keewaydin Island travel package?
You'll score amazing savings when you combine your hotels, flights and rental cars into a travel package. Not only that, booking everything in one spot just makes things easier. So why waste your time or money? Whether you're organizing a ritzy city getaway or a low-cost family break, check out our package deals today.
Can I choose my airline with a Keewaydin Island Expedia vacation package?
You certainly can. We have more than 550 airline partners across the globe, so fly with the carrier that best suits your budget and traveling style.
If I'm not able to travel, can I cancel my Keewaydin Island vacation package?
It's difficult to predict what the future holds, so it's good to know that you can cancel or change your Keewaydin Island vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

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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.