Winklers Vacations from $317

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Your Winklers Vacation

Your next big journey beckons with a vacation package to Winklers. Excitement, fun and nonstop great times — you're bound to find it in this neighborhood. Your trip to Winklers wouldn't be complete without a visit to big-name attractions nearby such as Fishing Pier Fort Myers Beach, Bunche Beach and Jungle Golf Ft. Myers. Stop dreaming and start doing. When you're ready to lock in your next vacation to Winklers, Expedia will help you get there.

The Latest Winklers Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Fort Myers Sanibel Gateway by IHG

Candlewood Suites Fort Myers Sanibel Gateway by IHG

3 out of 5
South Fort Myers
Save 100% on your flight
Price was $532, price is now $317 per person
$317
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
14.8/10 Exceptional! (1,002 reviews)
Great place to stay.

Reviewed on Nov 10, 2025

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $1,467, price is now $498 per person
$498
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
18.4/10 Exceptional! (1,001 reviews)
Great room, great location, great staff and great perks.

Reviewed on Nov 19, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $769, price is now $420 per person
$420
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
18.4/10 Exceptional! (704 reviews)
Property was lovely. View of the golf course from the balcony was nice!

Reviewed on Nov 19, 2025

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
Price was $946, price is now $542 per person
$542
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
16.4/10 Exceptional! (1,004 reviews)
The room was clean but it smells very musty like needed window to air it out.

Reviewed on Nov 14, 2025

Home2 Suites by Hilton Fort Myers Airport

Home2 Suites by Hilton Fort Myers Airport

3 out of 5
Save 100% on your flight
Price was $745, price is now $428 per person
$428
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
18/10 Exceptional! (398 reviews)
The hotel was very clean, cozy, and well-maintained, creating a comfortable and relaxing atmosphere from the moment I arrived. The staff was friendly and helpful, and the room had everything I needed for a pleasant stay. I especially appreciated how spacious and modern the suite felt. Overall, I would definitely stay here again and highly recommend it to anyone looking for a clean, comfortable, and welcoming place to stay.

Reviewed on Nov 2, 2025

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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(108 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

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
$204 nightly
The price is $228 total per night from Dec 7 to Dec 8
$228 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,641 reviews)
Very nice and clean resort!

Reviewed on Nov 17, 2025

Margaritaville Beach Resort Fort Myers
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
$189 nightly
The price is $210 total per night from Dec 14 to Dec 15
$210 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (1,917 reviews)
Great staff and clean

Reviewed on Nov 18, 2025

Naples Grande Beach Resort
Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

2.5 out of 5
1538 Cape Coral Pkwy E Cape Coral FL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Dec 16 to Dec 17
$89 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
Room was very clean, the staff were outstanding

Reviewed on Nov 17, 2025

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
See all 17,242 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Winklers

Fishing Pier Fort Myers Beach featuring a sandy beach and a bridge

Lynn Hall Memorial Park

4.5/5(786 reviews)

Walk over the water on a long pier that’s popular day and night for the breeze and fishing.

Lynn Hall Memorial Park
Bunche Beach featuring general coastal views and a 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
#kidsfun I wouldn't say feed the seagulls but there are so many nice restaurants and beach shops.

Castle Beach

Why not spend a lazy afternoon at Castle Beach during your trip to Fort Myers Beach?

Castle Beach

Things to do

Fort Myers Beach Sunset Excursion

Fort Myers Beach Sunset Excursion

$65
per adult
100% of travellers recommend
Fort Myers Beach Sunset Excursion
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

$70
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

$65
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
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.