Winkler Vacations from $293

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Your Winkler Vacation

Your next big journey is calling your name with a vacation package to Winkler. Fun, food and nothing but great times — you're sure to find it in this neighborhood. Kick off your trip to Winkler by checking out nearby attractions such as Edison and Ford Winter Estates, Imaginarium Hands - On Museum and Edison Mall. No matter what your dream Winkler vacation looks like, you can make it a reality with Expedia.

The Latest Winkler Vacation Packages

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
Price was $486, price is now $293 per person
$293
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,009 reviews)
Noisy air conditioning, had to turn of AC room 104

Reviewed on Oct 31, 2025

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $1,279, price is now $634 per person
$634
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,013 reviews)
Nice place very enjoyable

Reviewed on Nov 3, 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
Price was $1,620, price is now $926 per person
$926
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,003 reviews)
All aspects of this resort were excellent!

Reviewed on Nov 6, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,274, price is now $735 per person
$735
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (443 reviews)
every thong was fantastic specially the front desk

Reviewed on Nov 4, 2025

South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
Price was $1,530, price is now $917 per person
$917
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,008 reviews)
Great family moments created in this place

Reviewed on Nov 6, 2025

Where to stay in Winkler

Find the best Winkler areas and neighborhoods for the activities you enjoy most. Learn more about Winkler
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Iona

Iona might not have many top sights, but Cape Coral Yacht Club Beach and Key West Express are two attractions nearby that you can check out.

Find hotels in Iona

Winkler Hotel Deals

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
$209 nightly
The price is $234 total per night from Nov 19 to Nov 20
$234 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (1,599 reviews)
Amazing place

Reviewed on Nov 4, 2025

Margaritaville Beach Resort Fort Myers
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
$176 nightly
The price is $197 total per night from Nov 12 to Nov 13
$197 total
Nov 12 - Nov 13
Total with taxes and fees
8.8/10 Excellent! (1,025 reviews)
The new bar and staff are excellent! Place is still under construction over 4 out of 5

Reviewed on Nov 3, 2025

Lani Kai Beachfront Resort
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
$111 nightly
The price is $124 total per night from Nov 30 to Dec 1
$124 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (1,029 reviews)
Room was comfortable, neat and clean.

Reviewed on Nov 3, 2025

Hilton Garden Inn Ft Myers
See all 14,766 properties in Winkler
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
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Kid Friendly Vacations

Discover the most popular places to visit in Winkler

Edison Mall featuring signage

Edison Mall

4/5(41 reviews)

You can enjoy retail therapy at Edison Mall during your visit to Fort Myers. Attend a baseball game or discover the beautiful sunsets in this family-friendly area.

Edison Mall
Edison and Ford Winter Estates which includes a house and street scenes

Edison and Ford Winter Estates

4.5/5(594 reviews)

Explore the winter estates of two of the most famous men in American history. Tour their houses and gardens and learn more about their lives in the museum.

Edison and Ford Winter Estates
Barbara B Mann Hall featuring a pond

Barbara B Mann Hall

4.5/5(12 reviews)

You can get tickets for a performance at Barbara B Mann Hall on your trip to Fort Myers. Stroll along the beautiful beaches or discover the beautiful sunsets in this family-friendly area.

Barbara B Mann Hall

Things to do

Marco Island: 10,000 Islands Shelling Boat Tour

Marco Island: 10,000 Islands Shelling Boat Tour

$100
per adult
100% of travellers recommend
Marco Island: 10,000 Islands Shelling Boat Tour
Fort Myers Beach: Adults only BYOB Tiki Pub Sunset Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Sunset Cruise

$75
per adult
Fort Myers Beach: Adults only BYOB Tiki Pub Sunset Cruise
Historic Walking Tour of Fort Myers

Historic Walking Tour of Fort Myers

$26
per adult
100% of travellers recommend
Historic Walking Tour of Fort Myers
See all activities in Fort Myers
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.