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.

Landing Apartments Fort Myers near Olympia Pointe

$588

per person

Nov 11 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (9 reviews)

Great pool,comfortable room.

Reviewed on Mar 27, 2026

The Perry Hotel Naples

Save 100% on your flight

$642

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,163 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$4,161

per person

Dec 23 - Dec 30

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,004 reviews)

Landing Furnished Apartments Immokalee Road - Naples

Rural Estates

Save 100% on your flight

$827

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

8.4/10 Very Good! (5 reviews)

Landing Apartments Fort Myers - River District

Fort Myers River District

$661

per person

Nov 11 - Nov 16

found 1 day 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

$1,150

per person

Dec 17 - Dec 21

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

$7,156

per person

Dec 25 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (38 reviews)

The Ritz-Carlton, Naples

Pelican Bay

$4,358

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip flight included

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

9.2/10 Wonderful! (519 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

$580

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,006 reviews)

The Perry Hotel Naples

Save 100% on your flight

$642

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,163 reviews)

Sundial Beach Resort & Spa

Mid Island

$822

per person

Nov 13 - Nov 16

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

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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.

Casa Ybel Resort

Mid Island

Save 100% on your flight

$657

per person

Nov 14 - Nov 18

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (432 reviews)

The Lighthouse Resort Inn & Suites

$932

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,790 reviews)

NOT FAMILY FRIENDLY. But is a great place. Music last until 12 both nights. Tiki bar was Tiking. Tiki bar is nice. Room was clean, cold( great for Florida heat). Night stands need to be replaced. Very small. Shower was hot, when needed. Colby was wonderful!! Answered all of my questions, and was very friendly. Would stay again.

Reviewed on Oct 4, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$3,013

per person

Dec 29 - Jan 2

found 7 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,004 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.