Winkler Vacations from $434

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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.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $801, price is now $434 per person
$434
per person
Mar 17 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Erica was wonderful, she was very pleasant and very accommodating.

Reviewed on Jan 2, 2026

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $1,049, price is now $556 per person
$556
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
The staff at the counter are not friendly at all, the room was just clean.

Reviewed on Jan 6, 2026

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $2,024, price is now $1,142 per person
$1,142
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
A great place to stay. Very clean. Very professionally run. Great breakfast options included. Incredible work out facility. I’d highly recommend Innovation

Reviewed on Jan 3, 2026

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 $1,121, price is now $633 per person
$633
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,004 reviews)
Great hotel Great people and service. Very good breakfast

Reviewed on Jan 2, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,956, price is now $1,139 per person
$1,139
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
Nice rooms and amenities, clean. Need to improve food quality in all restaurants and the smell of food that is all over.

Reviewed on Jan 8, 2026

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

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
$179 nightly
The price is $200 total per night from Jan 11 to Jan 12
$200 total
Jan 11 - Jan 12
Total with taxes and fees
9/10 Wonderful! (1,082 reviews)
It was our first time there. Would go back.

Reviewed on Jan 6, 2026

Lani Kai Beachfront Resort
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
$381 nightly
The price is $425 total per night from Jan 10 to Jan 11
$425 total
Jan 10 - Jan 11
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Staff was very nice. A problem we had was their were 4 of us in the room and trying to get 4 towels and washcloths was a hard task, also coffee in room.

Reviewed on Jan 3, 2026

Marriott Sanibel Harbour Resort & Spa
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 refundable
$142 nightly
The price is $158 total per night from Jan 11 to Jan 12
$158 total
Jan 11 - Jan 12
Total with taxes and fees
9.2/10 Wonderful! (1,141 reviews)
Privacy with own balcony, great breakfast every morning and friendly stuff.

Reviewed on Jan 6, 2026

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
See all 15,059 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Winkler

Edison Mall featuring signage

Edison Mall

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

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
#BeachBound

Sanibel Harbour

Commune with nature and explore the great outdoors at Sanibel Harbour during your travels in Fort Myers. Stroll along the beautiful beaches or visit the spas in this romantic area.

Sanibel Harbour

Things to do

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
Everglades Day Safari from Sanibel, Fort Myers & Naples

Everglades Day Safari from Sanibel, Fort Myers & Naples

$225
per adult
Everglades Day Safari from Sanibel, Fort Myers & Naples
Close-up encounters with our beautiful Dolphins

Private Dolphin & Sightseeing Boat Day Tour

$185
per adult
Private Dolphin & Sightseeing Boat Day Tour
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.