Winkler Vacations from $334
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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.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,207, price is now $734 per person
$734
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
We had an excellent stay at La Playa Beach & Golf Resort in Naples. The location is hard to beat—the hotel is right on a beautiful stretch of beach, making it incredibly convenient to enjoy the Gulf without ever needing to leave the property.
The amenities were outstanding. We loved relaxing by the pool, the beach service was excellent, and everything was well maintained. The staff was friendly and attentive, helping make our stay feel truly relaxing and enjoyable.
If you’re looking for a beachfront resort with great amenities and a wonderful atmosphere, La Playa is an excellent choice. We would definitely stay here again.
Reviewed on Jun 29, 2026
Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $1,450, price is now $888 per person
$888
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (369 reviews)
We would most definitely stay at this resort again. We had a wonderful time. The only thing that I wish was included was the beach chairs and umbrellas. It was wonderful to have beach access right off the screened in patio along with your own faucet right at the steps to clean the sand off before entering your suite. Top notch place.
Reviewed on Jun 30, 2026
The Perry Hotel Naples
Save 100% on your flight
Price was $933, price is now $616 per person
$616
per person
Aug 15 - Aug 21
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (893 reviews)
Had an amazing time. Room was great. They upgraded me for free. Got two free drinks. Parking was free. Pools were amazing. Bars were wonderful. Food was gourmet. Staff was super friendly and answered all our questions. A boat takes you to an island with a beautiful beach for free. They had a ping pong table. The breakfast is not included but they have great food and drink options. Couldn’t be happier with my stay. Will definitely go back next time I visit Naples.
Reviewed on Jun 30, 2026
Landing Apartments near North Fort Myers
Hancock
Save 100% on your flight
Price was $1,037, price is now $689 per person
$689
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (68 reviews)
I would recommend it to all my friends that would be traveling to Florida it’s been great every time I stayed at landing condo never had any problems at all it’s was what they said it be clean friendly excellent place
Reviewed on Jun 17, 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
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$252 nightly
The price is $281 total per night from Jul 6 to Jul 7
$281 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (2,278 reviews)
"I had a great stay at Margaritaville! The resort has a fun, relaxing beach vibe, and the rooms are beautiful and very comfortable with a true vacation feel. The beach was very nice and just steps away. We also really enjoyed the pool area with a DJ playing music and a lively atmosphere. The drinks ..."
Reviewed on Jun 30, 2026
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
$147 nightly
The price is $164 total per night from Jul 2 to Jul 3
$164 total
Jul 2 - Jul 3
Total with taxes and fees
9/10 Wonderful! (1,681 reviews)
"You have to pay for all the amenities (parking, beach chairs and umbrella at the beach … Very low pressure for showering. The music very loud from 9 am to 10 pm , very nice balcony with ocean view but impossible to relax… I’ll not recommend for relaxing time."
Reviewed on Jun 30, 2026
Sanibel Island Beach Resort
1231 Middle Gulf Dr Sanibel FL
Fully refundableReserve now, pay when you stay
$274 nightly
The price is $303 total per night from Jul 2 to Jul 3
$303 total
Jul 2 - Jul 3
Total with taxes and fees
9.2/10 Wonderful! (2,070 reviews)
"The room and bath are clean and fresh each time we stay. Love the linens and bed. So comfortable!! Amenities are wonderful. Easy access to beach. Grounds and shrubbery are beautiful!!! Property is so well kept. Always hate to leave!!"
Reviewed on Jul 1, 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.
Stay near popular Winkler attractions
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
Fort Myers Dolphin & Manatee Kayak or Paddleboard Tour
$72
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.