Wing South Vacations from $250

Book a Hotel + Flight or Car together to unlock savings

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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $429, price is now $250 per person
$250
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
It was very clean, in a good location, has an outdoor pool, very pleasant staff.

Reviewed on Sep 6, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $1,468, price is now $664 per person
$664
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
The overall experience at the hotel was excellent.

Reviewed on Sep 2, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $944, price is now $553 per person
$553
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
I enjoyed the Hospitality and spa services and 2nd floor pool absolutely great experience.

Reviewed on Sep 6, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $686, price is now $405 per person
$405
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (515 reviews)
Very nice hotel. Good service and great rooms.

Reviewed on Aug 31, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $822, price is now $504 per person
$504
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
It's lovely and clean, but it opened in January; hopefully, it will stay that way in the future. The only issue for me was the prices at the rooftop bar. A glass of wine is $16 for a Sauvignon Blanc, and that bottle is $10 at Costco or Total Wine.

Reviewed on Sep 6, 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
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $229 total per night from Sep 8 to Sep 9
$229 total
Sep 8 - Sep 9
Total with taxes and fees
Naples Grande Beach Resort
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
$184 nightly
The price is $204 total per night from Sep 15 to Sep 16
$204 total
Sep 15 - Sep 16
Total with taxes and fees
Hilton Marco Island Beach Resort and Spa
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
$119 nightly
The price is $132 total per night from Sep 14 to Sep 15
$132 total
Sep 14 - Sep 15
Total with taxes and fees
Hyatt House Naples/5th Avenue
See all 10,626 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

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

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

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.