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.

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

$801

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (135 reviews)

We scheduled our stay for my wife's 60th birthday party. We had spoken to the hotel staff about how we were looking forward to celebrating by the rooftop pool.. THE ROOFTOP POOL WAS CLOSED THE ENTIRE TIME WE WERE THERE FOR A PRIVATE COMPANY PARTY. EXTREMELY DISAPPOINTED!!

Reviewed on Oct 25, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$4,756

per person

Dec 28 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Very helpful staff, great Gulf side room. Undergoing some renovation so only one elevator working but didn’t create too much of a problem. Great location, nice people.

Reviewed on Oct 25, 2026

The Perry Hotel Naples

Save 100% on your flight

$2,618

per person

Dec 28 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,224 reviews)

Landing Apartments Fort Myers - River District

Fort Myers River District

$884

per person

Jan 3 - Jan 10

found 1 day ago

Roundtrip flight included

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

7.6/10 Good! (8 reviews)

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$972

per person

Jan 14 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 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

$1,270

per person

Jan 14 - Jan 19

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,703 reviews)

Everything was fine except the first room they gave us was with cockroaches dead like 7 or 8 but we went back to the lobby and they were very nice and change our room. The other thing that we didn’t like was the beds, they are extremely hard. Everything else was fine. Very familiar and relaxing.

Reviewed on Oct 25, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$8,266

per person

Dec 28 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

The only downside was the pool was cold and wish they heated it since there was more of a coldfront here this week.

Reviewed on Oct 21, 2026

The Ritz-Carlton, Naples

Pelican Bay

$7,278

per person

Dec 28 - Jan 4

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.

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$577

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

$801

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (135 reviews)

Reviewed on Oct 25, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

$2,820

per person

Dec 27 - Dec 30

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Very helpful staff, great Gulf side room. Undergoing some renovation so only one elevator working but didn’t create too much of a problem. Great location, nice people.

Reviewed on Oct 25, 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.

Quality Inn Fort Myers Cape Coral

$289

per person

Jan 6 - Jan 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

7.6/10 Good! (465 reviews)

Manasota Key Resort

$927

per person

Jan 11 - Jan 15

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

9.4/10 Exceptional! (333 reviews)

We loved our stay. Thank you so much for the great hospitality

Reviewed on Oct 22, 2026

Tween Waters Island Resort & Spa

$748

per person

Dec 3 - Dec 7

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

Tween waters was absolutely wonderful! No complaints. The room was beautiful, the amenities were clean, and the staff was So helpful

Reviewed on Oct 25, 2026

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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.