Keewaydin Island Vacation Packages 2026 from $372

Keewaydin Island flight + hotel vacation packages

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

The Perry Hotel Naples

Save 100% on your flight

$372

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a beach shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy the a rooftop terrace.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

$653

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

Inn on Fifth

Old Naples

Save 100% on your flight

$458

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and perks like a free beach shuttle. Enjoy the a rooftop terrace and unwind at the bar/lounge and poolside bar.

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Save 100% on your flight

$613

per person

Aug 23 - Aug 30

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. Relax with a drink at one of the 2 poolside bars and enjoy the 2 hot tubs and 24-hour gym.

A Wave From it All

Siesta Isle

Save 100% on your flight

$1,620

per person

Sep 26 - Oct 2

found 7 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

This vacation home features 6 beach bars and an outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, barbecue grills, and a virtual front desk are also on offer.

Top Keewaydin Island hotels deals

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL

Free Cancellation

Reserve now, pay when you stay

$246 nightly

$273 total

Aug 10 - Aug 11

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this resort. Spend a day at the beach parasailing, or relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas.

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$154 total

Aug 3 - Aug 4

Total with taxes and fees

A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the outdoor pool and free buffet breakfast each morning.

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL

$197 nightly

$219 total

Jul 22 - Jul 23

Total with taxes and fees

A water park, 4 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Enjoy the 8 indoor pools and perks like free WiFi.

The Perry Hotel Naples

12155 Tamiami Trail N Naples FL

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$171 total

Jul 21 - Jul 22

Total with taxes and fees

Naples Bay Resort & Marina

1500 Fifth Ave S Naples FL

Free Cancellation

Reserve now, pay when you stay

$253 nightly

$281 total

Jul 16 - Jul 17

Total with taxes and fees

This smoke-free hotel features a full-service spa, a marina, and 4 restaurants. There's fun for all ages with a lazy river and a children's pool, and babysitting is an added bonus. Enjoy the 5 outdoor pools and free perks like WiFi in public areas and a beach shuttle.

Compass by Margaritaville Hotel Naples

4805 Tamiami Trl N Naples FL

Free Cancellation

Reserve now, pay when you stay

$132 nightly

$147 total

Jul 15 - Jul 16

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

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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.

Frequently asked questions

How much are vacation packages to Keewaydin Island?

Your vacation daydreams can all come true in Keewaydin Island from an impressive $372. Our package deals include flights and hotels, so you'll find booking is easy as pie. The only thing you'll have to worry about is having an incredible time.

Where can I get the best vacation package deals for Keewaydin Island?

There are fantastic Keewaydin Island package deals to be snapped up with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 worldwide properties? Keep this in mind when you're ready to check another place off your list.

Why should I purchase my Keewaydin Island vacation bundle with Travelocity?

Because life is an amazing journey, and we've got everything you could hope for to help you along the way. With our high-quality service and Price Match Guarantee, you can book with confidence. What's more, you can sleep easy while you're on the road knowing we've got your back with our 24/7 customer support.

Can I save on my Keewaydin Island car rental if I combine it with a hotel or flight?

With a Keewaydin Island vacation package, you can combine your car, flight and hotel bookings and save loads. If you'd love to see the best of this wonderful destination, why not check out Vizcaya Museum and Gardens? This top attraction is 100 mi from Keewaydin Island. With your own wheels, you'll be there belong long.

Which airport is best for Keewaydin Island?

Keewaydin Island has two airports you can fly to — Southwest Florida Intl. Airport (RSW) (30 mi away from the city center) and Naples Municipal Airport (APF) (6 mi away from central Keewaydin Island).