Keewaydin Island Vacation Packages 2026 from $548

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

$548

per person

Sep 5 - Sep 12

found 1 day ago

Roundtrip 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.

A Wave From it All

Siesta Isle

Save 100% on your flight

$1,722

per person

Sep 6 - Sep 13

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Casa Tiki

Hancock

Save 100% on your flight

$594

per person

Sep 13 - Sep 20

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

This vacation home features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. Luggage storage, laundry facilities, and barbecue grills are also on offer.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,141

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

Save 100% on your flight

$759

per person

Sep 30 - Oct 7

found 11 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free aparthotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. A coffee shop, a snack bar/deli, and a picnic area 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

$215 nightly

$239 total

Aug 19 - Aug 20

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

$139 nightly

$154 total

Aug 9 - Aug 10

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

$179 nightly

$199 total

Aug 11 - Aug 12

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

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$83 total

Aug 3 - Aug 4

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

The Perry Hotel Naples

12155 Tamiami Trail N Naples FL

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$176 total

Aug 3 - Aug 4

Total with taxes and fees

Pool

Pet friendly

JW Marriott Marco Island Beach Resort

400 S Collier Blvd Marco Island FL

Free Cancellation

Reserve now, pay when you stay

$599 nightly

$664 total

Aug 2 - Aug 3

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 $548. 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).