Winklers Vacation Packages

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Top Holiday Package Deals in Winklers

Price found within the past 48 hours. Click for updated prices.
Edison Beach House

Edison Beach House

3.5 out of 5
Price was CA $1,010, price is now CA $604 per person
CA $604
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,490 reviews)
First stay at Edison beach house having stayed numerous times at FMB. Lift out of order and on the 5th floor but the balcony view over the beach and sunsets were awesome. Carpet tired in places and air con very noisy otherwise only complaint was the smoking from other guests throughout out stay.

Reviewed on Sep. 4, 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 $4,007, price is now CA $1,784 per person
CA $1,784
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop 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

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $2,577, price is now CA $1,363 per person
CA $1,363
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
Location, service and amenities are excellent

Reviewed on Aug. 31, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was CA $1,262, price is now CA $734 per person
CA $734
per person
Oct 20 - Oct 27
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
Kind and helpful staff

Reviewed on Sep. 4, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,969, price is now CA $1,175 per person
CA $1,175
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
“My stay at this hotel exceeded my expectations. The room was spotless, the staff were attentive and welcoming, and the amenities made my stay very comfortable. I would definitely recommend it to others.”

Reviewed on Sep. 3, 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 $233 per night from Sep 29 to Sep 30
CA $233
CA $328 total
Sep 29 - Sep 30
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 $210 per night from Oct 6 to Oct 7
CA $210
CA $289 total
Oct 6 - Oct 7
includes taxes & fees
Margaritaville Beach Resort Fort Myers
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
12600 University Dr, Fort Myers, FL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Sep 12 to Sep 13
CA $148
CA $165 total
Sep 12 - Sep 13
includes taxes & fees
Hilton Garden Inn Ft Myers
See all 16,476 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 $604. 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

4/5(20 reviews)

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 lively bars.

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.