Keewaydin Island Vacation Packages 2026 from $743

Name: Inn on Fifth
Price range: $795 total

Keewaydin Island flight + hotel vacation packages

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

Hilton Garden Inn Ft Myers

Villas

Save 100% on your flight

$743

per person

Mar 1 - Mar 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

The Perry Hotel Naples

Save 100% on your flight

$1,655

per person

Mar 1 - Mar 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) 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

$896

per person

Apr 9 - Apr 14

just found

Roundtrip non-stop flight included

Hartford (BDL) 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.

South Seas Resort

Save 100% on your flight

$1,653

per person

Mar 1 - Mar 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) 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. Bring the family and enjoy the children's pool, waterslide, and kid-friendly dining.

Home2 Suites by Hilton Fort Myers Colonial Blvd

Save 100% on your flight

$857

per person

Mar 1 - Mar 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Top Keewaydin Island hotels deals

Naples Grande Beach Resort

475 Seagate Drive Naples FL

Free Cancellation

Reserve now, pay when you stay

$512 nightly

$569 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

Fairways Inn of Naples

103 Palm River Blvd Naples FL

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$164 total

Jan 21 - Jan 22

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

Inn on Fifth

699 5th Ave S Naples FL

Free Cancellation

Reserve now, pay when you stay

$716 nightly

$795 total

Jan 19 - Jan 20

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and perks like a free beach shuttle. Enjoy the a rooftop terrace and unwind at the bar/lounge and poolside bar.

Pool

Hot Tub

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL

$465 nightly

$516 total

Jan 18 - Jan 19

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

Marco Beach Ocean Suites

480 S Collier Blvd Marco Island FL

$264 nightly

$293 total

Jan 18 - Jan 19

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 Ritz-Carlton, Naples

280 Vanderbilt Beach Rd Naples FL

$1,359 nightly

$1,509 total

Feb 1 - Feb 2

Total with taxes and fees

A full-service spa, 5 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Relax with beach cabanas, sun loungers, and beach umbrellas. Bring the family and enjoy the children's club, children's pool, and arcade/game room.

Pool

Spa

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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.

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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 $743. 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).