Wing South Vacations from $268

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Your Wing South Vacation

Take the stress and hassle out of organizing your next break by booking a Wing South vacation package. Immerse yourself in the sounds and sights of this appealing neighborhood and experience what it has to offer. Your trip to Wing South wouldn't be complete without a stop at leading attractions nearby such as Mustang Course - Lely Resort, Hibiscus Golf Club and Florida Panther National Wildlife Refuge. Expedia will help turn your dream Wing South vacation into reality, no matter your budget or travel plans.

The Latest Wing South 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
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
8.2/10 Very Good! (1,001 reviews)
Close to shopping and eating

Reviewed on Jul 21, 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
Sep 25 - Sep 29
found 2 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

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.6/10 Exceptional! (2,186 reviews)
Had the absolute best time at Bellasera with my husband and three kids. The service at this resort is outstanding. We would love to give a shout out to Mike, the driver. He’d take us to and from the beach and always had great stories to share. My kids still talk about him few weeks later. We can’t wait to go back.

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 12 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
Great location and service !!!!!

Reviewed on Jul 21, 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 12 - Oct 18
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

Where to stay in Wing South

Find the best Wing South areas and neighborhoods for the activities you enjoy most. Learn more about Wing South
Naples Botanical Garden showing a garden and a pond

East Naples

4/5(171 area reviews)

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.

Find hotels in East Naples

Wing South Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
$171 nightly
The price is $190 total per night from Aug 12 to Aug 13
$190 total
Aug 12 - Aug 13
Total includes taxes and fees
9/10 Wonderful! (1,601 reviews)
"This is like home away from home! Spa services are an integral part of the beauty of this resort! Food and drinks are top notch, and having been there for several visits over the years its great to see familiar faces on staff and receive the best service! Cannot wait to go back!"

Reviewed on Jul 20, 2025

Naples Grande Beach Resort
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South, Naples, FL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $141 total per night from Aug 3 to Aug 4
$141 total
Aug 3 - Aug 4
Total includes taxes and fees
8.8/10 Excellent! (1,340 reviews)
"Awesome stay , they should tell you before hand , $27 a night parking"

Reviewed on Jul 19, 2025

Hyatt House Naples/5th Avenue
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd, Marco Island, FL
Fully refundableReserve now, pay when you stay
$260 nightly
The price is $289 total per night from Aug 10 to Aug 11
$289 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,457 reviews)
"everything was excellent!"

Reviewed on Jul 20, 2025

Hilton Marco Island Beach Resort and Spa
See all 10,570 properties in Wing South
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 Wing South

Naples Beach

Naples Beach

4.5/5(1,407 reviews)

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

Naples Beach
5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

4.5/5(45 reviews)

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South
Naples Pier featuring a sandy beach and landscape views as well as a large group of people

Naples Pier

4.5/5(1,161 reviews)

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Naples Pier

Things to do

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

$64
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

$70
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
Naples Florida: Downtown Electric Moped Tour

Naples Florida: Downtown Electric Moped Tour

$60
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Moped Tour
See all activities in Naples
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.