Keewaydin Island Vacation Packages for 2025

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Top Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
15.81 km from city center
Stay at this 4.5-star luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 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 ...
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South, Naples, FL
7.87 km from city center
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
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
Stay at this 4-star 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 ...
Hilton Naples

Hilton Naples

4 out of 5
5111 Tamiami Trl N, Naples, FL
15.55 km from city center
Stay at this 4-star business-friendly hotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Ritz-Carlton, Naples

The Ritz-Carlton, Naples

5 out of 5
280 Vanderbilt Beach Rd, Naples, FL
20.48 km from city center
Stay at this 5-star luxury resort in Naples. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Popular attractions Vanderbilt Beach and Barefoot ...
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
Stay at this 4-star business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
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 ...
Fairways Inn of Naples

Fairways Inn of Naples

3 out of 5
103 Palm River Blvd, Naples, FL
22.56 km from city center
Stay at this 3-star hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
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
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free WiFi, free parking, and a marina. Our guests praise the restaurant and the bar in our reviews. ...
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
Stay at this 4-star 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 ...
Trianon Bonita Bay

Trianon Bonita Bay

3.5 out of 5
3401 Bay Commons Dr, Bonita Springs, FL
31.09 km from city center
Stay at this 3.5-star family-friendly hotel in Bonita Springs. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the pool ...
Inn on Fifth

Inn on Fifth

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

Holiday Inn Express Hotel Naples Downtown - 5th Avenue

2.5 out of 5
7.66 km from city center
Book a stay at this golf hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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
Stay at this 4.5-star luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are ...
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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.

Spirit Airlines
Sat, Feb 21 - Sat, Feb 28
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$106 Roundtrip, found 11 hours ago
$106
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Sat, Feb 21 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Feb 28, priced at $106 found 11 hours ago
Frontier Airlines
Fri, Sep 12 - Tue, Sep 16
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, found 3 days ago
$112
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Hopkins Intl. to Southwest Florida Intl., returning Tue, Sep 16, priced at $112 found 3 days ago
United
Sun, Oct 19 - Fri, Oct 24
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select United flight, departing Sun, Oct 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Oct 24, priced at $130 found 1 day ago
JetBlue Airways
Tue, Oct 7 - Tue, Oct 14
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$137 Roundtrip, found 18 hours ago
$137
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Tue, Oct 7 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Tue, Oct 14, priced at $137 found 18 hours ago
Delta
Tue, Dec 2 - Tue, Dec 9
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Dec 2 from Logan Intl. to Southwest Florida Intl., returning Tue, Dec 9, priced at $147 found 3 days ago