Keewaydin Island Vacation Packages 2025/2026 from $293

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

$293

per person

Jan 26 - Jan 30

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. 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.

Matanzas Inn Bayside Resort and Marina

$405

per person

Jan 26 - Jan 30

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.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,740

per person

Jan 3 - Jan 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$409

per person

Jan 26 - Jan 30

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 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.

The Perry Hotel Naples

Save 100% on your flight

$834

per person

Jan 3 - Jan 10

found 1 day ago

Roundtrip non-stop 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.

Top Keewaydin Island hotels deals

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$92 total

Nov 30 - Dec 1

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

Reserve now, pay when you stay

$189 nightly

$210 total

Dec 14 - Dec 15

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. Family-friendly amenities include a waterslide and kid-friendly dining, along with tennis lessons.

Pool

Hot Tub

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL

Free Cancellation

Reserve now, pay when you stay

$252 nightly

$280 total

Dec 18 - Dec 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

Fairways Inn of Naples

103 Palm River Blvd Naples FL

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$109 total

Nov 23 - Nov 24

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

Marco Beach Ocean Suites

480 S Collier Blvd Marco Island FL

$193 nightly

$214 total

Nov 20 - Nov 21

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

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL

Free Cancellation

Reserve now, pay when you stay

$170 nightly

$189 total

Nov 25 - Nov 26

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

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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

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.

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.

Frequently asked questions

How much are vacation packages to Keewaydin Island?

Your vacation daydreams can all come true in Keewaydin Island from an impressive $293. 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).