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Keewaydin Island Vacation Packages

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Keewaydin Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
Price was $881, price is now $621 per person
$621
per person
Mar 1 - Mar 7
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Save 100% on your flight
Price was $2,007, price is now $1,173 per person
$1,173
per person
Mar 5 - Mar 13
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)
Stay at this condo in Punta Gorda. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage Museum are located nearby.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,438, price is now $1,545 per person
$1,545
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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 Barefoot Beach are located nearby.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,118, price is now $761 per person
$761
per person
Mar 9 - Mar 13
found 2 hours ago
Roundtrip flight included
Hartford (BDL) 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 Captiva Beach and Captiva Chapel By the Sea are located nearby.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $1,015, price is now $705 per person
$705
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $1,222, price is now $857 per person
$857
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this golf aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
Island Escape

Island Escape

2 out of 5
Save 100% on your flight
Price was $1,772, price is now $1,264 per person
$1,264
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this vacation home in Fort Myers Beach. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Key West Express and Bonita Springs Public Beach are located nearby.
Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach

Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach

3 out of 5
Save 100% on your flight
Price was $7,853, price is now $5,622 per person
$5,622
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Fort Myers (RSW)
Stay at this cottage in Marco Island. Enjoy free parking, private pools, and patios. Popular attractions Mackle Park and Marco Island Historical Museum are located nearby.

Keewaydin Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $856, price is now $541 per person
$541
per person
Mar 13 - Mar 16
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,157, price is now $780 per person
$780
per person
Apr 4 - Apr 8
found 6 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,118, price is now $761 per person
$761
per person
Mar 9 - Mar 13
found 2 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,189, price is now $809 per person
$809
per person
Apr 14 - Apr 18
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)

Keewaydin Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $1,503, price is now $916 per person
$916
per person
Apr 13 - Apr 18
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,858, price is now $1,109 per person
$1,109
per person
Apr 13 - Apr 18
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,438, price is now $1,545 per person
$1,545
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
Price was $3,238, price is now $2,068 per person
$2,068
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Feb 24 - Sat, Feb 28
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$61 Roundtrip, found 2 days ago
$61
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Feb 24 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Feb 28, priced at $61 found 2 days ago
Frontier Airlines
Sun, Feb 15 - Thu, Feb 26
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$84 Roundtrip, found 2 hours ago
$84
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Feb 15 from Philadelphia Intl. to Southwest Florida Intl., returning Thu, Feb 26, priced at $84 found 2 hours ago
Spirit Airlines
Tue, Mar 3 - Tue, Mar 10
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$101 Roundtrip, found 2 hours ago
$101
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Mar 3 from Logan Intl. to Southwest Florida Intl., returning Tue, Mar 10, priced at $101 found 2 hours ago
Frontier Airlines
Mon, Feb 23 - Fri, Feb 27
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Hopkins Intl. to Southwest Florida Intl., returning Fri, Feb 27, priced at $118 found 1 day ago