Wing South Holidays from £678

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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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was £889, price is now £678 per person
£678
per person
7 Nov - 12 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9.2/10 Wonderful! (598 reviews)
We always have a great time

Reviewed on 26 Aug 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
Price was £2,658, price is now £1,357 per person
£1,357
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LON) to Fort Myers (RSW)
8.8/10 Excellent! (1,003 reviews)
I loved the beachfront access

Reviewed on 27 Aug 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was £1,858, price is now £1,133 per person
£1,133
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
Hotel was fabulous. Modern look, clean a beautiful room. Staff was fantastic, friendly and helpful. Pool was great. The hotel is located right in the middle of things on 5th Avenue @Naples.

Reviewed on 4 Aug 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was £1,161, price is now £792 per person
£792
per person
7 Nov - 12 Nov
found 1 day ago
Return direct flight included
London (LHR) to Fort Myers (RSW)
9.6/10 Exceptional! (393 reviews)
Staff members more than excellent. The hotel perfect!!

Reviewed on 25 Aug 2025

Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
South End
Price was £1,333, price is now £1,060 per person
£1,060
per person
13 Oct - 19 Oct
found 1 day ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9/10 Wonderful! (859 reviews)
Pool is under loud construction. Was not told this was happening when booking. Gave us a room that should have been off limits to guests. Offered 20% refund, still waiting for it. not happy . the pool they send you too is 30 mins away and closes at 2pm.

Reviewed on 25 Aug 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
South Florida which includes a bay or harbour, a coastal town and a marina

Old Naples

3 out of top 10 points of interest in this area
4.5/5(44 area reviews)

The stunning beaches and popular shops are just a few highlights of Old Naples. Make a stop by Fifth Avenue South or Naples Beach while you're exploring the area.

Find hotels in Old Naples

Top hotels in Wing South

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
The price is £171 per night from 10 Sept to 11 Sept
£171
10 Sept - 11 Sept
includes taxes & fees
9/10 Wonderful! (1,664 reviews)
"Towels not as white as they should be. Housekeeping have to be requested"

Reviewed on 26 Aug 2025

Naples Grande Beach Resort
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S, Naples, FL
Fully refundableReserve now, pay when you stay
The price is £59 per night from 8 Sept to 9 Sept
£59
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very Good! (1,604 reviews)
"I really like the staff at this place This is my second stay here The only negative is there is no grassy area for a pet to utilize"

Reviewed on 22 Aug 2025

La Quinta Inn & Suites by Wyndham Naples Downtown
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 £105 per night from 2 Sept to 3 Sept
£105
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,423 reviews)
"Great"

Reviewed on 23 Aug 2025

Hyatt House Naples/5th Avenue
See all 10,587 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 £678, 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.

Popular places to visit

Naples Beach

Naples Beach

4.5/5(52 reviews)

Why not spend a care-free 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 featuring a city, street scenes and markets

Fifth Avenue South

4/5(3 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 beach and landscape views as well as a large group of people

Naples Pier

4.5/5(58 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

£47
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

£52
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
Naples Florida: Downtown Electric Moped Tour

Naples Florida: Downtown Electric Moped Tour

£52
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. Flight-inclusive packages are ATOL protected.