Keewaydin Island Vacation Packages 2026 from $556

Keewaydin Island flight + hotel vacation packages

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

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

$556

per person

May 23 - May 26

found 1 day 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 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. A coffee shop, a snack bar/deli, and a picnic area are also on offer.

Villa Marco Island

Save 100% on your flight

$1,256

per person

May 31 - Jun 7

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

An outdoor pool, free self parking, and laundry facilities are featured at this villa. WiFi in public areas is free. A terrace, a garden, and a grocery/convenience store are also on offer.

The Boat House

Olde Marco

Save 100% on your flight

$848

per person

May 1 - May 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a picnic area, and express check-in are also on offer.

Windward Passage Resort

$1,709

per person

May 20 - May 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features an outdoor pool and an outdoor tennis court. Enjoy the hot tub and perks like free self parking and free WiFi. The front desk is staffed around-the-clock and laundry facilities are on offer.

Bellasera Resort

Old Naples

Save 100% on your flight

$802

per person

May 13 - May 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This condo resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free valet parking. Enjoy the gym and perks like free self parking and a free beach shuttle.

Top Keewaydin Island hotels deals

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL

$474 nightly

$526 total

Apr 12 - Apr 13

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

The Perry Hotel Naples

12155 Tamiami Trail N Naples FL

Free Cancellation

Reserve now, pay when you stay

$324 nightly

$360 total

Mar 14 - Mar 15

Total with taxes and fees

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.

Pool

Pet friendly

Naples Grande Beach Resort

475 Seagate Drive Naples FL

Free Cancellation

$540 nightly

$600 total

Mar 31 - Apr 1

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

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$221 total

Mar 29 - Mar 30

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

$113 nightly

$125 total

Apr 5 - Apr 6

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

Compass by Margaritaville Hotel Naples

4805 Tamiami Trl N Naples FL

Free Cancellation

Reserve now, pay when you stay

$227 nightly

$252 total

Apr 2 - Apr 3

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.

Pool

Breakfast included

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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

5th Avenue Shopping District which includes markets, street scenes and a city

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(1,407 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.

Vanderbilt Beach

4.5/5(313 reviews)

If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.

Frequently asked questions

How much are vacation packages to Keewaydin Island?

Your vacation daydreams can all come true in Keewaydin Island from an impressive $556. 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).