Keewaydin Island Vacation Packages 2026 from $278

Name: Fairways Inn of Naples
Price range: $164 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

$278

per person

Mar 14 - Mar 17

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.

Hilton Garden Inn Ft Myers

Villas

Save 100% on your flight

$288

per person

Mar 14 - Mar 17

found 1 day ago

Roundtrip 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.

Tween Waters Island Resort & Spa

Save 100% on your flight

$585

per person

Mar 9 - Mar 13

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.

The Perry Hotel Naples

Save 100% on your flight

$1,480

per person

Mar 22 - Mar 28

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.

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

Save 100% on your flight

$909

per person

Mar 22 - Mar 28

found 1 day 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.

Top Keewaydin Island hotels deals

Marco Beach Ocean Suites

480 S Collier Blvd Marco Island FL

$264 nightly

$293 total

Jan 21 - Jan 22

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

$240 nightly

$267 total

Jan 25 - Jan 26

Total with taxes and fees

Pool

Pet friendly

Naples Grande Beach Resort

475 Seagate Drive Naples FL

Free Cancellation

$414 nightly

$460 total

Feb 4 - Feb 5

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

JW Marriott Marco Island Beach Resort

400 S Collier Blvd Marco Island FL

$829 nightly

$920 total

Jan 21 - Jan 22

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

Fairways Inn of Naples

103 Palm River Blvd Naples FL

$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

The Ritz-Carlton, Naples

280 Vanderbilt Beach Rd Naples FL

$1,559 nightly

$1,731 total

Jan 21 - Jan 22

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

Don't see what you're looking for?

See all available properties in Keewaydin Island

View all properties

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

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.

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.

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.

Frequently asked questions

How much are vacation packages to Keewaydin Island?

Your vacation daydreams can all come true in Keewaydin Island from an impressive $278. 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).