Wing South Holidays from £858

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Wing South Holiday

Take the stress and hassle out of planning your next break by booking a Wing South holiday package. Immerse yourself in the sights and sounds of this captivating neighbourhood and enjoy all it has to offer. When it's time to take in the sights, you'll find plenty of awesome attractions nearby including Flamingo Island Course - Lely Resort, Mustang Course - Lely Resort and Hibiscus Golf Club. Visit one, two or all during your trip to Wing South. Whatever your dream Wing South holiday may look like, you can turn it into reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was £1,120, price is now £858 per person
£858
per person
22 Aug - 29 Aug
found 1 day ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9.6/10 Exceptional! (912 reviews)
The room was very specious but the shower could’ve been cleaner as it has moldy edges. The restaurants were good but not enough options for kids. The staff were always very helpful and kind.

Reviewed on 6 Jul 2026

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Price was £1,497, price is now £1,086 per person
£1,086
per person
21 Sept - 27 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
8.8/10 Excellent! (369 reviews)
Everything was great

Reviewed on 5 Jul 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was £1,230, price is now £955 per person
£955
per person
21 Sept - 27 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
Their office hours end at the same time as when the check-in starts. So they left a letter on the office door with my last name on it when we arrived before dinner. Opened the envelope and got the code to open the safe next to the office door to get the keys. Opened the room only to find the bed sheets were on the floor. The restroom was a mess left by the previous guest. Looks like they were in the middle of cleaning the room and left in a hurry. Tried calling their off-hours number, but no one answered. The Wi-Fi code didn't work. I had to use my phone hotspot to get the computer online with Expedia. Spent over an hour with Expedia live chat and phone call. We were too hungry. We were forced to book a room at a non-motel hotel for the night; I don't want to repeat the same experience.

Reviewed on 6 Jul 2026

GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
South Island
Price was £1,380, price is now £1,088 per person
£1,088
per person
21 Sept - 27 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9.4/10 Exceptional! (953 reviews)
We have stayed here before. We love how big the rooms are. The pool is always clean. Their is always someone cleaning around the property

Reviewed on 27 Jun 2026

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Price was £1,192, price is now £959 per person
£959
per person
21 Sept - 27 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9/10 Wonderful! (1,681 reviews)
The location is great. You can walk by the beach directly from the elevators. We asked for our room to be cleaned several times but they mixed up the request and finally nobody came. They put music all day and is quite loud. Other than that, the place is great if you want to go on a few beach days. There are also some restaurants at walking distance from the hotel.

Reviewed on 6 Jul 2026

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
A pink and white orchid plant with a rocky background.

East Naples

5/5(2 area reviews)

Beaches, shopping and restaurants are some highlights of East Naples. Make a stop by Fifth Avenue South or Naples Botanical Garden while you're exploring.

Find hotels in East Naples

Top hotels in Wing South

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
The price is £198 per night from 2 Aug to 3 Aug
£198
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,879 reviews)
"Our 24th anniversary was celebrated at the Hilton and the hotel and staff were fantastic. We were completely replenished with the rest and relaxation provided. Thanks to all."

Reviewed on 6 Jul 2026

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
The price is £116 per night from 2 Aug to 3 Aug
£116
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,857 reviews)
"El hotel es espectacular, muy buena atención. Solo mejoraría el desayuno"

Reviewed on 6 Jul 2026

Hyatt House Naples/5th Avenue
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
The price is £165 per night from 8 Jul to 9 Jul
£165
8 Jul - 9 Jul
includes taxes & fees
9.4/10 Exceptional! (1,013 reviews)
"All very good staff with nice attitude .. a lot of activities for kids. Good food..ice cream..dunkin dunots inside the hotel.i really recommend it"

Reviewed on 5 Jul 2026

Great Wolf Lodge Naples
See all 10,809 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Wing South travel package cost?
Our Wing South packages, which start at just £858, are the best way to save big bucks. Handpick your preferred hotels, flights and more to create a personalized getaway.
If I'm not able to travel, can I cancel my Wing South travel package?
Whether it's your hotel or flight, you can cancel or alter it. Locked in your Wing South travel package in the last 24 hours? You may be able to make changes at no cost. For bookings made more than 24 hours ago, you may be charged a fee by your hotel, airline or car rental company. For more details, browse our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Wing South?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you cash too. A Wing South travel package makes it simple to arrange your ideal trip. With more than 550 airlines across the world to pick from, finding convenient flights that suit your schedule won't be difficult. In addition to that, we've got over 1,000,000 properties globally to select from. Talk about choice! Whatever your budget, Expedia will help show you the world.
Does Expedia offer Book Now, Pay Later Wing South holidays?
We sure do. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in instalments. Simply choose the payment plan that suits best during checkout and take away the stress of budgeting for your next trip. Be sure to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that fit all budgets, so you can escape on that well-earned holiday sooner.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Wing South?
Travellers come from all over the world to experience Barefoot Beach and Naples Pier in Wing South. Book a room close to these terrific attractions to make sightseeing a breeze.
What are the top hotels in Wing South?
Get your trip off to a flying start by booking a room at Naples Grande Beach Resort. It's one of most popular properties in Wing South. Another leading option is Hampton Inn - Naples - I-75.
How far in advance should I book my Wing South holiday?
It can be difficult to know exactly when the best time is to book your Wing South holiday. But typically the earlier you book, the lower the prices. Sometimes, you can lock in your flights and hotels nearly a year prior to departure. If you're hoping for a last-minute getaway, no need to fret! There are incredible deals popping up on Expedia all the time.
What does an Expedia Wing South travel package include?
Hotels, car rentals and flights — we bring you all the best deals. All you'll have to do is decide on your ideal combination. After you've made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it easy to customize an exciting Wing South escape.
What should I know before booking a Wing South travel package?
Whether it's adventure or relaxation you're seeking, a Wing South travel package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Wing South Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our travel packages give you the freedom to pick from available flights, hotels and activities that fit your needs.

Things to do

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

£43
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

£59
per adult
Naples: Sightseeing and Dining Cruises
Everglades National Park: Pontoon Boat Tour & Boardwalk

Everglades National Park: Pontoon Boat Tour & Boardwalk

£45
per adult
100% of travellers recommend
Everglades National Park: Pontoon Boat Tour & Boardwalk
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. Flight-inclusive packages are ATOL protected.