Keewaydin Island Vacation Packages for 2026

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Keewaydin Island Flight + Hotel packages

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

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,042, price is now $739 per person
$739
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.
It was fabulous

Reviewed on Jun 30, 2026

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,169, price is now $759 per person
$759
per person
Oct 25 - Oct 30
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) 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 Sanibel Island Lighthouse are located nearby.
Casa Ybel was amazing! We only went for 5 days, but we're considering making it our return resort anytime we visit Sanibel. The room was clean, and all the features were great for cooking anytime we wanted. It's right down the street from Jerry's Groceries and a lot of food places, shops, etc so the location is super convenient. For people looking to shell, even with it not being "peak season" since we went in June, it was still great for getting some really cool finds. For anyone considering staying at Casa Ybel, I highly recommend it!

Reviewed on Aug 3, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,252, price is now $830 per person
$830
per person
Oct 25 - Oct 30
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) 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.
If you are disabled or handicapped DO NOT stay here. The management was rude and hurtful. We have stay there almost 30 years. Something bad is going on there.

Reviewed on Aug 4, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,455, price is now $969 per person
$969
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Delnor-Wiggins Pass State Park are located nearby.
Great place to stay. Everything you need is on the property

Reviewed on Aug 4, 2026

Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

4 out of 5
Save 100% on your flight
Price was $1,322, price is now $925 per person
$925
per person
Oct 6 - Oct 13
found 4 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Myers (RSW)
Book a stay at this business-friendly apartment in Naples. Enjoy free WiFi, a rooftop terrace, and a fitness center. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Close by beach and 5th avenue

Reviewed on Jul 10, 2026

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

5 out of 5
Mid Island
Save 100% on your flight
Price was $1,556, price is now $1,135 per person
$1,135
per person
Oct 25 - Oct 30
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) to Fort Myers (RSW)
Book a stay at this luxury aparthotel in Sanibel. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the property condition in our reviews. Popular attractions Sanibel Island Southern Beach and Sanibel Island Lighthouse are located nearby.
Good

Reviewed on Aug 1, 2026

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Top Hotel Deals

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd Marco Island FL
17.55 km from city center
Book a stay at this beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in ...
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South Naples FL
7.88 km from city center
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
15.52 km from city center
Book a stay at this family-friendly hotel in Naples. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Popular attractions Paradise Coast Sports Compex and ...
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

3 out of 5
1555 5th Ave S Naples FL
7.62 km from city center
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
12155 Tamiami Trail N Naples FL
23.49 km from city center
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Delnor-Wiggins Pass ...
JW Marriott Marco Island Beach Resort

JW Marriott Marco Island Beach Resort

4 out of 5
400 S Collier Blvd Marco Island FL
16.83 km from city center
Book a stay at this beach resort in Marco Island. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff and the property ...
Naples Bay Resort & Marina

Naples Bay Resort & Marina

4 out of 5
1500 Fifth Ave S Naples FL
7.66 km from city center
Book a stay at this spa hotel in Naples. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

4 out of 5
4805 Tamiami Trl N Naples FL
15.06 km from city center
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Hilton Naples

Hilton Naples

4 out of 5
5111 Tamiami Trl N Naples FL
15.52 km from city center
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Inn on Fifth

Inn on Fifth

4 out of 5
699 5th Ave S Naples FL
7.99 km from city center
Book a stay at this spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
1221 5th Ave S Naples FL
8.1 km from city center
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
480 S Collier Blvd Marco Island FL
17.15 km from city center
Book a stay at this beach resort in Marco Island. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

5 out of 5
851 Gulf Shore Blvd N Naples FL
9.93 km from city center
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Fifth Avenue South and Naples Beach ...
Trianon Bonita Bay

Trianon Bonita Bay

3.5 out of 5
3401 Bay Commons Dr Bonita Springs FL
31.09 km from city center
Book a stay at this family-friendly hotel in Bonita Springs. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the pool ...
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
9891 Gulf Shore Dr Naples FL
21.53 km from city center
Book a stay at this luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Nov 2 - Wed, Nov 11
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$98 Roundtrip, found 5 days ago
$98
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Nov 2 from Hopkins Intl. to Southwest Florida Intl., returning Wed, Nov 11, priced at $98 found 5 days ago
Delta
Sat, Oct 3 - Tue, Oct 6
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$189 Roundtrip, found 4 days ago
$189
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 3 from Logan Intl. to Southwest Florida Intl., returning Tue, Oct 6, priced at $189 found 4 days ago
Sun Country Airlines
Tue, Dec 8 - Tue, Dec 15
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Tue, Dec 8 from Minneapolis - St. Paul Intl. to Southwest Florida Intl., returning Tue, Dec 15, priced at $227 found 3 days ago
American Airlines
Sat, Sep 19 - Sat, Sep 26
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$239 Roundtrip, found 2 hours ago
$239
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Sep 19 from Minneapolis - St. Paul Intl. to Southwest Florida Intl., returning Sat, Sep 26, priced at $239 found 2 hours ago
United
Sat, Sep 19 - Sat, Sep 26
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$239 Roundtrip, found 2 hours ago
$239
Roundtrip
found 2 hours ago
Select United flight, departing Sat, Sep 19 from Minneapolis - St. Paul Intl. to Southwest Florida Intl., returning Sat, Sep 26, priced at $239 found 2 hours ago