Winkler Vacations from $402
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Your Winkler Vacation
Your next big journey is calling your name with a vacation package to Winkler. Fun, food and nothing but great times — you're sure to find it in this neighborhood. Kick off your trip to Winkler by checking out nearby attractions such as Edison and Ford Winter Estates, Imaginarium Hands - On Museum and Edison Mall. No matter what your dream Winkler vacation looks like, you can make it a reality with Expedia.
The Latest Winkler Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Save 100% on your flight
Price was $1,413, price is now $847 per person
$847
per person
May 14 - May 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.8/10 Exceptional! (1,114 reviews)
Unit was extremely nice, great layout and very updated!
Reviewed on Mar 8, 2026
The Perry Hotel Naples
Save 100% on your flight
Price was $1,031, price is now $692 per person
$692
per person
May 25 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (664 reviews)
This hotel has a “Miami” vibe…excellent Asian Fusion restaurant on the top floor and two pool options. There is another great restaurant next door to the hotel, The Bay House. Parking is very easy at the hotel. The riverfront rooms we stayed in (the first one on the sixth floor under the kitchen was very noisy and they moved us to the seventh floor which was much quieter) were modern and had a nice balcony with a chairs and a table. We would definitely stay at this hotel again and look forward to trying their other properties.
Reviewed on Mar 9, 2026
Hilton Marco Island Beach Resort and Spa
South End
Save 100% on your flight
Price was $1,296, price is now $883 per person
$883
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,714 reviews)
Hotel is nice! Manager didn’t help me when I wanted pool and beach view which I requested when I booked it! He didn’t even try to look to maje me happy I had a room overlooking the top of a roof. Other than that everything was great.
Also there’s a store on the Hilton a yogurt is like $7.00. A coffee is $5 triple or quadruple the price in the supermarket. Crazy!!
Reviewed on Mar 9, 2026
GullWing Beach Resort
South Island
Save 100% on your flight
Price was $1,903, price is now $1,303 per person
$1,303
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (933 reviews)
Place was every thing we could ask for
Reviewed on Mar 7, 2026
Where to stay in Winkler
Find the best Winkler areas and neighborhoods for the activities you enjoy most. Learn more about Winkler
Iona
While visiting Iona, you might make a stop by sights like Estero Bay Preserve State Park and Tribby Arts Center.
Winkler Hotel Deals
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E Cape Coral FL
Fully refundable
$101 nightly
The price is $113 total per night from Apr 5 to Apr 6
$113 total
Apr 5 - Apr 6
Total with taxes and fees
9.2/10 Wonderful! (1,292 reviews)
The room was clean and the property is an older hotel that is kept in very good shape. The pool area is great and most of the staff were friendly and welcoming. Unfortunately, the morning front desk clerk, Mallory, was consistently unpleasant and somewhat condescending during my stay. Everyone else ...
Reviewed on Mar 10, 2026
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$490 nightly
The price is $547 total per night from Mar 12 to Mar 13
$547 total
Mar 12 - Mar 13
Total with taxes and fees
9/10 Wonderful! (1,931 reviews)
It's 5'o clock somewhere! Honestly, this is the best place I've ever stayed. Colorful, smells good, lots of fun activities and the steak and egg breakfast was heavenly! Started the day with a wonderful massage. Maybe one last dip in the beach before I leave! It was a great weekend away!
Reviewed on Mar 9, 2026
Sanibel Island Beach Resort
1231 Middle Gulf Dr Sanibel FL
Fully refundableReserve now, pay when you stay
$424 nightly
The price is $470 total per night from Apr 8 to Apr 9
$470 total
Apr 8 - Apr 9
Total with taxes and fees
9.2/10 Wonderful! (1,667 reviews)
This is a lovely place. You step out onto the beach from the tiki bar and pool. Staff was very helpful. There’s a restaurant on site and was very good. The only thing I would recommend is if you can stay on the 2nd floor, there isn’t much in the way of sound proofing between the floors. You could ...
Reviewed on Mar 9, 2026
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.
Discover the most popular places to visit in Winkler
Edison Mall
You can enjoy retail therapy at Edison Mall during your visit to Fort Myers. Attend a baseball game or discover the beautiful sunsets in this family-friendly area.
Edison and Ford Winter Estates
Explore the winter estates of two of the most famous men in American history. Tour their houses and gardens and learn more about their lives in the museum.
Bell Tower Shops
You can search for that perfect souvenir at Bell Tower Shops during your visit to Fort Myers. Discover the beautiful sunsets and top-notch restaurants in this family-friendly area.
Things to do
Marco Island: 10,000 Islands Shelling Boat Tour
$100
per adult
100% of travellers recommend
Historic Walking Tour of Fort Myers
$30
per adult
100% of travellers recommend
Everglades Day Safari from Sanibel, Fort Myers & Naples
$225
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.