Keewaydin Island Vacation Packages 2026 from $289

Name: Inn on Fifth
Price range: $601 total

Keewaydin Island flight + hotel vacation packages

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

Hyatt Place Fort Myers/at The Forum

The Forum

Save 100% on your flight

$289

per person

Mar 9 - Mar 12

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

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

Hilton Garden Inn Ft Myers

Villas

$606

per person

Feb 17 - Feb 24

found 16 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$368

per person

Mar 9 - Mar 12

found 15 hours 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.

Courtyard by Marriott Fort Myers Cape Coral

Save 100% on your flight

$564

per person

Feb 17 - Feb 24

found 16 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

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

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$1,143

per person

Feb 6 - Feb 10

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

3 outdoor pools, a lazy river, and a gym are all featured at this smoke-free aparthotel. 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.

Top Keewaydin Island hotels deals

Naples Grande Beach Resort

475 Seagate Drive Naples FL

$512 nightly

$569 total

Jan 19 - Jan 20

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

$148 nightly

$164 total

Jan 11 - Jan 12

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

$541 nightly

$601 total

Jan 26 - Jan 27

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

$439 nightly

$488 total

Jan 22 - Jan 23

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

$172 nightly

$191 total

Jan 11 - Jan 12

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

$1,080 nightly

$1,199 total

Jan 8 - Jan 9

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.

Popular places to visit

Vanderbilt Beach

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.

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

Fifth Avenue South

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.

Naples Beach

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.

Frequently asked questions

How much are vacation packages to Keewaydin Island?

Your vacation daydreams can all come true in Keewaydin Island from an impressive $289. 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).