Keewaydin Island Vacation Packages 2026 from $543

Keewaydin Island flight + hotel vacation packages

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

Chadwick Cove Resort & Marina

$543

per person

Aug 17 - Aug 21

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

This smoke-free condo features a marina and 7 restaurants. Dine at the beachfront restaurant and relax with beach umbrellas. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas.

Tween Waters Island Resort & Spa

Save 100% on your flight

$686

per person

Aug 12 - Aug 16

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.

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$709

per person

Jul 15 - Jul 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach

South End

Save 100% on your flight

$4,110

per person

Jul 24 - Jul 29

found 2 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

$589

per person

Jul 17 - Jul 21

found 4 hours ago

Roundtrip flight included

Boston (BOS) 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

$279 nightly

$309 total

Jun 8 - Jun 9

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

Fairways Inn of Naples

103 Palm River Blvd Naples FL

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$94 total

Jun 17 - Jun 18

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.

Pool

Breakfast included

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$94 total

Jun 14 - Jun 15

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

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL

Free Cancellation

Reserve now, pay when you stay

$186 nightly

$206 total

Jun 8 - Jun 9

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

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$179 total

Jun 14 - Jun 15

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

Hilton Naples

5111 Tamiami Trl N Naples FL

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$131 total

Jun 1 - Jun 2

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free valet parking. Enjoy the 24-hour gym and perks like free self parking and a free beach shuttle.

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.

Popular places to visit

Fifth Avenue South

4.5/5(45 reviews)

During your trip to Naples, you can find the perfect gifts to bring home at Fifth Avenue South. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA

Naples Beach

4.5/5(1,422 reviews)

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

Naples Pier

4.5/5(1,175 reviews)

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Frequently asked questions

How much are vacation packages to Keewaydin Island?

Your vacation daydreams can all come true in Keewaydin Island from an impressive $543. 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).