Keewaydin Island Adventure Vacations 2026

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Top Adventure vacation packages in Keewaydin Island

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

Wiggins Pass Chalet

$510

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (292 reviews)

Been there before and the rates are good minutes from the beach

Reviewed on Oct 12, 2026

The Perry Hotel Naples

Save 100% on your flight

$639

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$751

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (123 reviews)

Staff were very polite and helpful other than when promotional items were attempted to be redeemed. Water stations were not available as stated. Very nice accommodations.

Reviewed on Oct 14, 2026

Lighthouse Resort and Club

East End

Save 100% on your flight

$1,234

per person

Nov 28 - Dec 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

No reviews

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$2,839

per person

Dec 29 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

The was very clean. Every day. The staff very friendly . The beach awesome lady

Reviewed on Oct 13, 2026

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5* Adventure vacations in Keewaydin Island

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

Sundial Beach Resort & Spa

Mid Island

$1,277

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

The room was clean but pretty bare for a condo u it. The bed we had has pretty hard. The couch was stiff as a board. The bathroom only had one sink and the only mirror in the whole place. The Staff were great. Beach view was great. Only ate breakfast once at the restaurant and it was not that good and very expensive. Should have know it was not as good as we were the only ones in there.

Reviewed on Oct 15, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$3,415

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

This was our first time at Four Seasons and I might say it will not be our last. Everything was amazing, The staff throughout were excellent.

Reviewed on Oct 12, 2026

The Ritz-Carlton Naples, Tiburón

$3,103

per person

Dec 25 - Dec 30

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (684 reviews)

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3 Night Adventure vacations in Keewaydin Island

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

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

$450

per person

Dec 3 - Dec 6

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (123 reviews)

Staff were very polite and helpful other than when promotional items were attempted to be redeemed. Water stations were not available as stated. Very nice accommodations.

Reviewed on Oct 14, 2026

The Perry Hotel Naples

Save 100% on your flight

$970

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$2,839

per person

Dec 29 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

The was very clean. Every day. The staff very friendly . The beach awesome lady

Reviewed on Oct 13, 2026

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See all available trips from Columbus to Keewaydin Island

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4 Night Adventure vacations in Keewaydin Island

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

Tween Waters Island Resort & Spa

Save 100% on your flight

$806

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

The Perry Hotel Naples

Save 100% on your flight

$837

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$3,145

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

The was very clean. Every day. The staff very friendly . The beach awesome lady

Reviewed on Oct 13, 2026

Don't see what you're looking for?

See all available trips from Columbus to Keewaydin Island

View all trips

How can I book the best Keewaydin Island adventure trips?

Choose your own adventure in Keewaydin Island, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Keewaydin Island family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Keewaydin Island. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Keewaydin Island adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Keewaydin Island adventure vacation for couples?

Book a Keewaydin Island couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Keewaydin Island?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Keewaydin Island with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.