Name: Inn on Fifth
Price range: $788 total
Rating: 9.2

Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Keewaydin Island vacation packages

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

Hilton Garden Inn Ft Myers

Villas

Save 100% on your flight

$457

per person

Feb 16 - Feb 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

The staff at the counter are not friendly at all, the room was just clean.

Reviewed on Jan 6, 2026

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$663

per person

Apr 2 - Apr 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,001 reviews)

Erica was wonderful, she was very pleasant and very accommodating.

Reviewed on Jan 2, 2026

Innovation Hotel

Save 100% on your flight

$1,142

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (527 reviews)

A great place to stay. Very clean. Very professionally run. Great breakfast options included. Incredible work out facility. I’d highly recommend Innovation

Reviewed on Jan 3, 2026

The Perry Hotel Naples

Save 100% on your flight

$836

per person

Feb 27 - Mar 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (477 reviews)

Nice rooms and amenities, clean. Need to improve food quality in all restaurants and the smell of food that is all over.

Reviewed on Jan 8, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$882

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Beautiful property with everything one could possibly need for a get-away.

Reviewed on Jan 6, 2026

Don't see what you're looking for?

See all available trips from Columbus to Keewaydin Island

View all trips

Discover the most popular places to visit in Keewaydin Island

Vanderbilt Beach

If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.

5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Naples Beach

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

What to do in Keewaydin Island

Sunset Tour in Naples Bay on a New Godfrey- All included

Naples Sunset Cruise - Complimentary Charcuterie and wine

$110

per adult

100% of travellers recommend

Best of Marco Dolphin Tour

$100

per adult

Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

$127

per adult

See all activities in Keewaydin Island

Keewaydin Island Hotel Deals

Naples Grande Beach Resort

475 Seagate Drive Naples FL

Fully refundable

$512 nightly

$569 total

Jan 19 - Jan 20

Total with taxes and fees

8.8/10 Excellent! (2,003 reviews)

The Signature King Suite was wonderful! Spacious with an amazing view, 2 mini fridges, and a super comfy bed. Beach, pool, and service were excellent. Would definitely recommend this property!!

Reviewed on Jan 6, 2026

Fairways Inn of Naples

103 Palm River Blvd Naples FL

Fully refundableReserve now, pay when you stay

$139 nightly

$154 total

Jan 11 - Jan 12

Total with taxes and fees

9.4/10 Exceptional! (1,155 reviews)

Quiet place with a lovely backyard.

Reviewed on Jan 6, 2026

Inn on Fifth

699 5th Ave S Naples FL

Fully refundableReserve now, pay when you stay

$709 nightly

$788 total

Jan 19 - Jan 20

Total with taxes and fees

9.2/10 Wonderful! (1,006 reviews)

Restaurants and shopping all within walking distance!

Reviewed on Jan 5, 2026

See all 10,842 properties in Keewaydin Island

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.