Keewaydin Island Vacation Packages 2026 from $493

Keewaydin Island flight + hotel vacation packages

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

Lehigh Resort Club

Joel

Save 100% on your flight

$493

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

2 outdoor tennis courts, an outdoor pool, and a hot tub are all featured at this smoke-free aparthotel. Bring the family and enjoy the mini golf, children's pool, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

South Seas

Save 100% on your flight

$856

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free resort features a private beach, a golf course, and a water park. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. You'll find 5 restaurants and 6 outdoor pools on site, along with a bar/lounge to unwind.

The Perry Hotel Naples

Save 100% on your flight

$718

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Shell Island Beach Club

East End

Save 100% on your flight

$1,057

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This aparthotel's 2 outdoor pools and outdoor tennis court are among the featured amenities. Enjoy the 2 hot tubs and get free self parking. A picnic area and barbecue grills are also provided.

Tween Waters Island Resort & Spa

Save 100% on your flight

$930

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free resort features a private beach, a full-service spa, and a marina. Family-friendly amenities include a children's pool and kid-friendly dining, along with kayaking. Free self parking is free for guests, and you can enjoy a meal in one of the 3 restaurants.

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

$218 nightly

$241 total

Aug 31 - Sep 1

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.

Pool

Hot Tub

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$160 total

Sep 7 - Sep 8

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.

Pool

Hot Tub

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL

$177 nightly

$196 total

Aug 20 - Aug 21

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.

Pool

Hot Tub

The Perry Hotel Naples

12155 Tamiami Trail N Naples FL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$147 total

Aug 23 - Aug 24

Total with taxes and fees

Pool

Pet friendly

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$74 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

JW Marriott Marco Island Beach Resort

400 S Collier Blvd Marco Island FL

Free Cancellation

Reserve now, pay when you stay

$410 nightly

$455 total

Aug 23 - Aug 24

Total with taxes and fees

A full-service spa, 5 restaurants, and 3 outdoor pools are all featured at this smoke-free resort. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Bring the family and enjoy the children's club, children's pool, and kid-friendly dining.

Pool

Hot Tub

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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 $493. 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).