Winklers Vacation Packages

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Top Holiday Package Deals in Winklers

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Price was CA $981, price is now CA $595 per person
CA $595
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.2/10 Very Good! (1,011 reviews)
Property was good. . Shopwer drains poorly standing in water all the time

Reviewed on Sep. 8, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $4,656, price is now CA $2,044 per person
CA $2,044
per person
Nov 29 - Dec 6
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
The overall experience at the hotel was excellent.

Reviewed on Sep. 2, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was CA $1,193, price is now CA $628 per person
CA $628
per person
Nov 18 - Nov 25
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
Over all a good stay and great price. Only issue would be the mattress was old lumpy , came home with back pain.

Reviewed on Sep. 8, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $3,743, price is now CA $2,140 per person
CA $2,140
per person
Nov 29 - Dec 6
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
They know how to make you feel special. The service was incredible; everyone is very, very friendly. The hotel is beautiful, very quiet, and centrally located just a few minutes from the beach. If you want a place to relax, this is the one. We will definitely be back.

Reviewed on Sep. 8, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $2,637, price is now CA $1,528 per person
CA $1,528
per person
Nov 29 - Dec 6
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
nice and very clean, comfortable room, quit at night around the pool feel good

Reviewed on Sep. 8, 2025

Where to stay in Winklers

Find the best Winklers areas and neighborhoods for the activities you enjoy most. Learn more about Winklers
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Mid Island

1 out of top 10 points of interest in this area
4.5/5(4 area reviews)

While visiting Mid Island, you might make a stop by sights like Estero Boulevard Beach and Sterling Ave Beach.

Find hotels in Mid Island

Winklers Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundableReserve now, pay when you stay
The price is CA $242 per night from Sep 9 to Sep 10
CA $242
CA $338 total
Sep 9 - Sep 10
includes taxes & fees
Naples Grande Beach Resort
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
The price is CA $216 per night from Sep 9 to Sep 10
CA $216
CA $295 total
Sep 9 - Sep 10
includes taxes & fees
Margaritaville Beach Resort Fort Myers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Sep 16 to Sep 17
CA $132
CA $179 total
Sep 16 - Sep 17
includes taxes & fees
Lani Kai Beachfront Resort
See all 16,546 properties in Winklers
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winklers vacation package cost?
Go from wondering to wandering with our Winklers vacation packages, which start from a low CA $595. Handpick the flights and hotels that fit your travel plans. Then, add on a couple of enriching experiences for a one-of-a-kind getaway.
How do I get a cheap travel package to Winklers?
Browse and book everything all in one place with our Winklers vacation packages. You'll find bargains on hotels, flights, tours and more that'll keep your budget happy and your adventurousness alive. And, with more than 550 air carriers and 1,000,000 properties around the world to select from, you'll have endless opportunities to mix and match.
Where should I stay in Winklers?
With fascinating attractions such as Key West Express and Fishing Pier Fort Myers Beach in this area, look for a hotel situated near either of them. Bunche Beach is another sight that visitors flock to.
How far in advance should I book my Winklers vacation?
While not all air carriers advertise tickets early, customers are usually able to start comparing international flights on Expedia up to a year in advance. This is when you'll score some fantastic deals. If you're purchasing tickets last minute, you could still be in luck. Sometimes the lowest prices appear only weeks before departure.
What does an Expedia Winklers travel package include?
Expedia has everything you need to organize your Winklers getaway, but how your package is structured depends on you. Select from any combination of hotels, rental cars and flights. Searching for some tours or activities to keep you on the go? Once you've made your booking, you can add them on too. No matter your style, there's a deal to meet your needs.
What should I know before booking a Winklers travel package?
Discover deals that match your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your break. You'll save precious dollars just for combining your bookings. Whether you're going on an adventure in the snow or drinking cocktails on a beach, your dream vacation is only clicks away.
Can I choose my airline with a Winklers Expedia vacation package?
With a vacation package, you're in charge. Whether you're eager to fly to Winklers in economy or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines across the world.
If I'm not able to travel, can I cancel my Winklers vacation package?
You can cancel your Winklers booking if your plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

Discover the most popular places to visit in Winklers

Bunche Beach

Bunche Beach

Find a relatively obscure beach in a popular area of sand, warm water and a fascinating variety of coastal life. You’ll be thankful for the uncrowded space.

Bunche Beach
Lynn Hall Memorial Park

Lynn Hall Memorial Park

Why not spend a carefree afternoon at Lynn Hall Memorial Park during your travels in Fort Myers Beach? Amble around this family-friendly area's seaside and enjoy its top-notch restaurants.

Lynn Hall Memorial Park

Key West Express

Explore the waterfront in Fort Myers Beach with a trip to Key West Express. Discover the area's beautiful sunsets and lively bars.

Key West Express

Things to do

Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

CA $89
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

CA $82
per adult
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

CA $90
per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
See all activities in Fort Myers Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.