Keewaydin Island Beach Vacations 2026

Top Beach vacation packages in Keewaydin Island

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

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Save 100% on your flight

$605

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (3,419 reviews)

Beautiful location on the harbor! Highly recommend the harbor view room! There was an issue with my bill but after one phone call it was resolved! Will be back again!

Reviewed on Oct 15, 2026

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)

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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$802

per person

Dec 15 - Dec 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

I love everything about this hotel

Reviewed on Oct 13, 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

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5* Beach 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 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (684 reviews)

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3 Night Beach 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 7 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)

Lighthouse Resort and Club

East End

$692

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Fort Myers (RSW)

No reviews

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4 Night Beach vacations in Keewaydin Island

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

The Suites at Fishermen’s Village

Punta Gorda Isles

Save 100% on your flight

$753

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip flight included

Rockford (RFD) to Fort Myers (RSW)

9.8/10 Exceptional! (1,330 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

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How do I book the best Keewaydin Island beach vacation packages?

Life’s a beach when you dive into our brilliant Keewaydin Island beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Keewaydin Island?

A rental steps from the shore creates an amazingly affordable Keewaydin Island beach vacation. Seaside sojourns during low season start from $450. Prices and availability are subject to change. Additional terms may apply.

When should I book a Keewaydin Island beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Keewaydin Island?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Keewaydin Island beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Keewaydin Island vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Keewaydin Island beach vacation deals?

Sort your search results by deals to delight in amazing Keewaydin Island beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Keewaydin Island beach trip with free cancellation and/or flexible dates?

Just like the Keewaydin Island tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Keewaydin Island beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Keewaydin Island. (OK, maybe not that last part.)