Winklers Vacation Packages

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Top Holiday Package Deals in Winklers

Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was CA $1,448, price is now CA $1,007 per person
CA $1,007
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
Staff is fantastic, beautiful property!

Reviewed on May 5, 2026

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 $3,032, price is now CA $1,708 per person
CA $1,708
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9/10 Wonderful! (1,001 reviews)
Nice, high end facility with friendly staff. Check in was easy, check out was easy, going to the beach was easy… very relaxing stay.

Reviewed on May 4, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,681, price is now CA $1,084 per person
CA $1,084
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9.4/10 Exceptional! (776 reviews)
Everything was terrific from the beautiful rooms, 2 pools, excellent and helpful staff to the breakfast bar in the morning. There are shuttles by van and boat to the beaches abs other locations. The new Tigress restaurant and outdoor bar were a perfect way to end the day.

Reviewed on May 3, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was CA $2,427, price is now CA $1,661 per person
CA $1,661
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 reviews)
👏👏wonderful resort .. loved the available bikes

Reviewed on Apr 24, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was CA $1,808, price is now CA $1,277 per person
CA $1,277
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Fort Myers (RSW)
9/10 Wonderful! (846 reviews)
The resort is wonderful. Beware the high pressure sale to join the Hyatt Vacation Club. That made our stay less than we hoped for.

Reviewed on May 5, 2026

Where to stay in Winklers

Find the best Winklers areas and neighborhoods for the activities you enjoy most. Learn more about Winklers
Sunset on the island of Sanibel.Florida.USA

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 Castle Beach and Estero Boulevard Beach.

Find hotels in Mid Island

Winklers Hotel Deals

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 $272 per night from May 27 to May 28
CA $272
CA $372 total
May 27 - May 28
includes taxes & fees
9/10 Wonderful! (2,071 reviews)
The place was very nice my wife and I love it

Reviewed on May 7, 2026

Margaritaville Beach Resort Fort Myers
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr Sanibel FL
Fully refundableReserve now, pay when you stay
The price is CA $318 per night from Jun 1 to Jun 2
CA $318
CA $388 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (1,868 reviews)
The resort was very cute. The rooms were basic, but well maintained. Everything functioned properly and was comfortable. The pool and bar were very nice areas. The staff at the bar were very helpful and kind. It was nice to have a seashell washing station and an outdoor shower for washing off before ...

Reviewed on May 6, 2026

Sanibel Island Beach Resort
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 $198 per night from May 11 to May 12
CA $198
CA $251 total
May 11 - May 12
includes taxes & fees
9/10 Wonderful! (1,461 reviews)
Beautiful view but being on the second floor above the bar, wasn’t our choice but no one asked if this location would work for us either. It was very noisy.

Reviewed on May 7, 2026

Lani Kai Beachfront Resort
See all 17,792 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.
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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 $1,007. 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
Palm trees at Fort Myers Beach Bowditch Point Park, Florida USA

Bowditch Point Park

You can take time to visit Bowditch Point Park during your travels to Fort Myers Beach. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.

Bowditch Point Park

Things to do

Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

CA $88
per adult
100% of travellers recommend
Dolphin Wildlife Cruise Fort Myers Beach
Clear Kayak Guided Eco Tour in North Naples

Clear Kayak Guided Eco Tour in North Naples

CA $123
per adult
100% of travellers recommend
Clear Kayak Guided Eco Tour in North Naples
Guided Kayak Eco Tour - Bunche Beach

Guided Kayak Eco Tour - Bunche Beach

CA $96
per adult
98% of travellers recommend
Guided Kayak Eco Tour - Bunche Beach
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.