Search Deals onKeewaydin Island Vacation Packages
Keewaydin Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
Save 100% on your flight
Price was $476, price is now $298 per person
$298
per person
Oct 16 - Oct 18
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Delnor-Wiggins Pass State Park and Vanderbilt Beach are located nearby.
!!!
Reviewed on Sep 2, 2026
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,506, price is now $806 per person
$806
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Bowman's Beach and Captiva Beach are located nearby.
The Lighthouse Resort Inn & Suites
Save 100% on your flight
Price was $962, price is now $596 per person
$596
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Casa Ybel Resort
Save 100% on your flight
Price was $1,040, price is now $662 per person
$662
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Sanibel Island Southern Beach and Bowman's Beach are located nearby.
The property is super convenient the beaches across the street a volleyball pool and then a huge lighted pool. The rooms were very clean older but clean and very comfortable. Mine felt like a little apartment tiki bar downstairs is great. The food is good. The drinks were good. They do play music until about midnight so if you don’t like music till that time, this isn’t the place for you lol. We will definitely stay here again.
Reviewed on Aug 30, 2026
Resort Harbour Properties
Save 100% on your flight
Price was $1,547, price is now $1,007 per person
$1,007
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo in Fort Myers. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
The property was clean and absolutely gorgeous. The pictures honestly didn't do it justice. The hospitality was great! The communication was top notch, but they weren't too much at all. Great privacy! Beach was steps away from the elevator. The location was wonderful! It was secluded but everything we needed was very close by. Sanibel Island was a 10 minute drive at most! We are only going to stay at this property in the future.
Reviewed on Aug 11, 2026
Mariners Boathouse by Coolvacay
Save 100% on your flight
Price was $1,254, price is now $820 per person
$820
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Pleasant stay. Staff friendly and attentive. Very relaxing stay. The view of the beach is a plus.
Reviewed on Aug 5, 2026
Windward Passage Resort
Save 100% on your flight
Price was $1,098, price is now $729 per person
$729
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Marriott Sanibel Harbour Resort & Spa
Save 100% on your flight
Price was $1,233, price is now $830 per person
$830
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Keewaydin Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Keewaydin Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Sep 25 - Fri, Oct 9
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$125 Roundtrip, found 17 hours ago
$125
Roundtrip
found 17 hours ago
Fri, Dec 11 - Mon, Dec 14
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$152 Roundtrip, found 19 hours ago
$152
Roundtrip
found 19 hours ago
Sun, Dec 6 - Sun, Dec 13
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$159 Roundtrip, found 11 hours ago
$159
Roundtrip
found 11 hours ago
Wed, Oct 28 - Sat, Oct 31
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$189 Roundtrip, just found
$189
Roundtrip
just found
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