Winkler Vacations from $403

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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 $775, price is now $403 per person
$403
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
We loved the location. The space was very clean and large. We will definitely be staying here again.

Reviewed on Jan 16, 2026

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was $1,170, price is now $565 per person
$565
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Good staff. Quality location

Reviewed on Jan 12, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $2,396, price is now $1,256 per person
$1,256
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
The place was really nice. The amenities such as several pools, jacuzzies, dry and wet saunas, adjacent to golf course, ferry shuttle to a beautiful beach made for a very relaxing time. Just what the doctor ordered. We had some problems with our room, AC in our room broke and needed to be fixed, blow dryer was broken. Lazy river was down for the week. The Concierges seemed reluctant to help at times, as if they were told not to let patrons take advantage. Ex. We missed the shuttle to the island by a minute and the concierge was like oh well your tough luck attitude rather than.... how can I make it happen for you.

Reviewed on Jan 15, 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 $972, price is now $513 per person
$513
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip 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

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,317, price is now $739 per person
$739
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Beautiful property with everything one could possibly need for a get-away.

Reviewed on Jan 6, 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
$195 nightly
The price is $218 total per night from Jan 19 to Jan 20
$218 total
Jan 19 - Jan 20
Total with taxes and fees
9/10 Wonderful! (1,097 reviews)
Great location, fun atmosphere lots of fun amenities!

Reviewed on Jan 11, 2026

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
$268 nightly
The price is $296 total per night from Jan 25 to Jan 26
$296 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (1,525 reviews)
Staff was great. Room was clean

Reviewed on Jan 12, 2026

Sanibel Island Beach 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
$401 nightly
The price is $448 total per night from Jan 18 to Jan 19
$448 total
Jan 18 - Jan 19
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Our balcony had the best view of Sanibel Island and Harbour.

Reviewed on Jan 14, 2026

Marriott Sanibel Harbour Resort & Spa
See all 15,141 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.