Winkler Vacations from $439

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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 $788, price is now $439 per person
$439
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)
Erica was wonderful, she was very pleasant and very accommodating.

Reviewed on Jan 2, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $2,848, price is now $1,486 per person
$1,486
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
The first room had a wet carpet. We were put in another room. This property could use some updating…

Reviewed on Jan 11, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,318, price is now $774 per person
$774
per person
Apr 5 - Apr 10
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

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,124, price is now $683 per person
$683
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
Everything was great

Reviewed on Jan 12, 2026

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,340, price is now $833 per person
$833
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,554 reviews)
Nice place. Right on the beach and walking to restaurants.

Reviewed on Jan 12, 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
$186 nightly
The price is $208 total per night from Jan 14 to Jan 15
$208 total
Jan 14 - Jan 15
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
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
$391 nightly
The price is $436 total per night from Jan 14 to Jan 15
$436 total
Jan 14 - Jan 15
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
$170 nightly
The price is $190 total per night from Jan 18 to Jan 19
$190 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (1,159 reviews)
Dry nice

Reviewed on Jan 11, 2026

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
See all 15,099 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
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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
#BeachBound

Sanibel Harbour

5/5(2 reviews)

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.