Keewaydin Island Adventure Vacations 2026

Top Adventure vacation packages in Keewaydin Island

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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$792

per person

Dec 15 - Dec 20

found 2 days ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

They staff always goes above and beyond. It is a wonderful hotel with beautiful views.

Reviewed on Oct 9, 2026

The Perry Hotel Naples

Save 100% on your flight

$832

per person

Dec 15 - Dec 20

found 2 days 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

$2,908

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)

Landing Furnished Apartments Immokalee Road - Naples

Rural Estates

Save 100% on your flight

$865

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.4/10 Very Good! (5 reviews)

Landing Apartments Fort Myers - River District

Fort Myers River District

$1,384

per person

Dec 27 - Jan 2

found 21 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Fort Myers (RSW)

7.6/10 Good! (8 reviews)

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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

$1,179

per person

Dec 14 - Dec 19

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$3,992

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

This resort was amazing!!

Reviewed on Oct 9, 2026

The Ritz-Carlton, Naples

Pelican Bay

$5,844

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (520 reviews)

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3 Night Adventure vacations in Keewaydin Island

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

Wiggins Pass Chalet

$640

per person

Jan 5 - Jan 8

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

9.6/10 Exceptional! (292 reviews)

The Perry Hotel Naples

Save 100% on your flight

$1,332

per person

Dec 30 - Jan 2

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

$1,384

per person

Jan 5 - Jan 8

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

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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

$652

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$743

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,800 reviews)

The room was adequate but very noisy—from 10 am until 11 pm there was music blaring. And no escaping it.

Reviewed on Oct 10, 2026

The Perry Hotel Naples

$1,340

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Keewaydin Island

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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.