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
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.2/10 Very Good! (1,001 reviews)
The room, breakfast and front desk receptionist were awesome. The one downfall was when room service opened the door to the room the morning at 10 am of us leaving and asking what time we were leaving granted check our time is 12 pm.

Reviewed on Jul. 19, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
per person
Aug 30 - Sep 6
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
Service was excellent

Reviewed on Jul. 19, 2025

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Park Shore
Save 100% on your flight
per person
Aug 30 - Sep 6
found 19 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,583 reviews)
This is like home away from home! Spa services are an integral part of the beauty of this resort! Food and drinks are top notch, and having been there for several visits over the years its great to see familiar faces on staff and receive the best service! Cannot wait to go back!

Reviewed on Jul. 20, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
per person
Aug 30 - Sep 6
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
A very nice hotel in the heart of downtown Naples. Clean modern rooms, attentive staff and a sunny pool deck. Naples’ best dining steps from your door.

Reviewed on Jul. 9, 2025

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.6/10 Excellent! (1,020 reviews)
It was what I expected, Room was big, clean, and the beds very comfortable. The room was supposed to be non-smoking, well...

Reviewed on Jul. 19, 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 refundable
The price is CA $195 per night from Aug 10 to Aug 11
CA $195
CA $278 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,591 reviews)
Need some entertainment
"Hotel is so relaxing, the only issue is no entertainment at all, just the beach and the pool"

Reviewed on Jul. 16, 2025

Naples Grande 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 $263 per night from Jul 21 to Jul 22
CA $263
CA $354 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"None"

Reviewed on Jul. 18, 2025

Lani Kai Beachfront Resort
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 $277 per night from Aug 19 to Aug 20
CA $277
CA $344 total
Aug 19 - Aug 20
includes taxes & fees
9/10 Wonderful! (1,224 reviews)
"Beach house as close and easy to get into town"

Reviewed on Jul. 19, 2025

Sanibel Island Beach Resort
See all 16,250 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 $330. 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 top-notch restaurants.

Key West Express

Things to do

Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

CA $84
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

CA $89
per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

CA $96
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
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.