Keewaydin Island Vacation Packages 2026 from $479

Keewaydin Island flight + hotel vacation packages

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

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$479

per person

Apr 10 - Apr 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

3 outdoor pools, a lazy river, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

Save 100% on your flight

$1,058

per person

Mar 2 - Mar 9

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

A marina and a restaurant are featured at this smoke-free condo resort. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$528

per person

Apr 18 - Apr 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a picnic area, and luggage storage are also on offer.

The Perry Hotel Naples

Save 100% on your flight

$994

per person

Mar 12 - Mar 16

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.

Tween Waters Island Resort & Spa

Save 100% on your flight

$682

per person

Apr 1 - Apr 5

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

Marco Beach Ocean Suites

480 S Collier Blvd Marco Island FL

$281 nightly

$312 total

Jan 29 - Jan 30

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this resort. WiFi in public areas is free. A garden, a free grocery shopping service, and luggage storage are also on offer.

Free WiFi

Air conditioning

The Perry Hotel Naples

12155 Tamiami Trail N Naples FL

Free Cancellation

Reserve now, pay when you stay

$374 nightly

$416 total

Feb 1 - Feb 2

Total with taxes and fees

Pool

Pet friendly

JW Marriott Marco Island Beach Resort

400 S Collier Blvd Marco Island FL

$1,389 nightly

$1,541 total

Feb 1 - Feb 2

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

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$177 total

Jan 28 - Jan 29

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

Naples Grande Beach Resort

475 Seagate Drive Naples FL

Free Cancellation

$575 nightly

$638 total

Feb 1 - Feb 2

Total with taxes and fees

A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the 15 outdoor tennis courts and free perks like WiFi in public areas and a beach shuttle.

Pool

Hot Tub

Bayfront Inn Fifth Avenue

1221 5th Ave S Naples FL

$224 nightly

$249 total

Jan 28 - Jan 29

Total with taxes and fees

A marina and an outdoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.

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

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Frequently asked questions

How much are vacation packages to Keewaydin Island?

Your vacation daydreams can all come true in Keewaydin Island from an impressive $479. 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).