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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.
Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Save 100% on your flight
Price was $1,097, price is now $746 per person
$746
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this aparthotel in Fort Myers. Enjoy free WiFi, free parking, and a fitness center. Popular attractions JetBlue Park at Fenway South and Six Mile Cypress Slough Preserve are located nearby.
Very Clean

Reviewed on Sep 9, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,167, price is now $1,379 per person
$1,379
per person
Nov 16 - Nov 22
found 18 hours 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 Delnor-Wiggins Pass State Park and Vanderbilt Beach are located nearby.
Shutter never works, rooftop bar staff is horrible

Reviewed on Sep 24, 2026

Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
Save 100% on your flight
Price was $1,606, price is now $1,037 per person
$1,037
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $3,822,303, price is now $2,498,976 per person
$2,498,976
per person
Dec 4 - Dec 11
found 1 day 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 Bowman's Beach and Captiva Beach are located nearby.

Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was $1,263, price is now $841 per person
$841
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this apartment in Fort Myers. Enjoy in-room washers/dryers, an in-room coffeemaker, and air conditioning. Popular attractions JetBlue Park at Fenway South and Calusa Nature Center and Planetarium are located nearby.
This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 2026

Landing Furnished Apartments minutes from Downtown Fort Myers

Landing Furnished Apartments minutes from Downtown Fort Myers

3 out of 5
Save 100% on your flight
Price was $1,419, price is now $968 per person
$968
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this apartment in North Fort Myers. Enjoy an outdoor pool, a fitness center, and an in-room coffeemaker. Popular attractions Art of the Olympians Museum and Caloosa Sound Amphitheater are located nearby.
I enjoyed my stay. It was clean and roomy. They proved complimentary laundry pods, dish washer pods, dish soap etc. I enjoyed sitting on the balcony drinking my coffee. The pool and pool area was beautiful. I wish, they'd give one access code for the whole stay not asign one each day. I'd stay there again.

Reviewed on Sep 21, 2026

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,418, price is now $971 per person
$971
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,165, price is now $798 per person
$798
per person
Dec 4 - Dec 11
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 Estero Boulevard Beach are located nearby.
Very clean and the staff was great

Reviewed on Sep 25, 2026

Keewaydin Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Olde Marco Island Inn and Suites

Olde Marco Island Inn and Suites

3 out of 5
Olde Marco
Price was $647, price is now $462 per person
$462
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,673, price is now $1,093 per person
$1,093
per person
Dec 8 - Dec 12
found 4 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was $814, price is now $574 per person
$574
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Spinnaker Inn of Naples

Spinnaker Inn of Naples

2 out of 5
Price was $697, price is now $499 per person
$499
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Keewaydin Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Olde Marco Island Inn and Suites

Olde Marco Island Inn and Suites

3 out of 5
Olde Marco
Save 100% on your flight
Price was $1,022, price is now $671 per person
$671
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,118, price is now $1,233 per person
$1,233
per person
Dec 1 - Dec 8
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Save 100% on your flight
Price was $1,606, price is now $1,037 per person
$1,037
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip 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 $3,822,303, price is now $2,498,976 per person
$2,498,976
per person
Dec 4 - Dec 11
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.

Breeze Airways
Sat, Jan 23 - Sat, Feb 6
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Jan 23 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Feb 6, priced at $152 found 3 days ago
Frontier Airlines
Sun, Nov 15 - Sat, Dec 5
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 15 from Hopkins Intl. to Southwest Florida Intl., returning Sat, Dec 5, priced at $163 found 1 day ago
Frontier Airlines
Mon, Feb 8 - Sat, Feb 13
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 8 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Sat, Feb 13, priced at $177 found 1 day ago
Delta
Wed, Oct 28 - Sat, Oct 31
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$189 Roundtrip, found 8 hours ago
$189
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Oct 28 from Logan Intl. to Southwest Florida Intl., returning Sat, Oct 31, priced at $189 found 8 hours ago