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

$676

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (292 reviews)

The Perry Hotel Naples

Save 100% on your flight

$1,100

per person

Dec 10 - Dec 14

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

$2,759

per person

Dec 19 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$843

per person

Dec 18 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Landing Apartments Fort Myers - River District

Fort Myers River District

$829

per person

Nov 8 - Nov 15

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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

$1,124

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,700 reviews)

Tiki bar and restaurants were excellent and very good prices for excellent food. All staff were so helpful. So much to do. Rooms were spacious and comfy

Reviewed on Oct 1, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$3,118

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

The Ritz-Carlton Naples, Tiburón

$3,451

per person

Dec 29 - Jan 2

found 20 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.

Hyatt Vacation Club at Coconut Cove, Bonita Springs

$554

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.2/10 Wonderful! (1,013 reviews)

Beautiful place, nice amenities. My only complaint is that it is a time-share location, and they will beat you to death to get you to join. Very annoying. We wanted a vacation, not a sales pitch.

Reviewed on Oct 6, 2026

The Perry Hotel Naples

Save 100% on your flight

$813

per person

Dec 19 - Dec 22

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$592

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Don't see what you're looking for?

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.

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$527

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,013 reviews)

Beautiful place, nice amenities. My only complaint is that it is a time-share location, and they will beat you to death to get you to join. Very annoying. We wanted a vacation, not a sales pitch.

Reviewed on Oct 6, 2026

The Perry Hotel Naples

Save 100% on your flight

$1,100

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Casa Ybel Resort

Mid Island

Save 100% on your flight

$538

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (439 reviews)

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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.