Winklers Vacations from $245

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
8.6/10 Excellent! (1,010 reviews)
Property is a little old

Reviewed on Jul 16, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
Service was excellent

Reviewed on Jul 19, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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

GreenLinks Golf Villas at Lely Resort

GreenLinks Golf Villas at Lely Resort

3 out of 5
Save 100% on your flight
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.4/10 Exceptional! (521 reviews)
We have stayed many times. Rooms a little older and not so fresh now but a great place to stay .

Reviewed on May 2, 2025

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.6/10 Exceptional! (2,186 reviews)
Loved the property, the condos are really nice. House keeping does an amazing job in maintaining the rooms. We used the pool, we used the beach chairs and towels. Everything worked out perfectly for us a family of 6.

Reviewed on Jul 16, 2025

Where to stay in Winklers

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

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

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$172 nightly
The price is $191 total per night from Aug 12 to Aug 13
$191 total
Aug 12 - Aug 13
Total includes taxes and fees
9/10 Wonderful! (1,596 reviews)
"Great hotel, nice room and restaurants with a beautiful sunset view from hotel and beach. Check in and checkout- we took almost 1 hour in lind, 2 people at fromt desk for the whole resort."

Reviewed on Jul 18, 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
$231 nightly
The price is $258 total per night from Jul 21 to Jul 22
$258 total
Jul 21 - Jul 22
Total includes taxes and fees
8.4/10 Very Good! (1,012 reviews)
"Debería de tener más diversión"

Reviewed on Jul 19, 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
$224 nightly
The price is $247 total per night from Aug 18 to Aug 19
$247 total
Aug 18 - Aug 19
Total includes taxes and fees
9/10 Wonderful! (1,217 reviews)
"Right on the beach. Updated rooms. A/C needs to be cleaned more often."

Reviewed on Jul 18, 2025

Sanibel Island Beach Resort
See all 16,259 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

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
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
#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

Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

$62
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Fort Myers Beach Sunset Excursion

Fort Myers Beach Sunset Excursion

$60
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
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.