Wing South Holidays

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    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.
  • Exterior
    Aug 2 - Aug 10

    THE Palmview AND Sandpiper Inns + Flight

    Mid Island
    8 nights
    3.5 star property
    9.4/10 - Exceptional (212 reviews)
    "This place was a huge disappointment and absolutely not what I expected based on the Expedia rating. The unit was tiny, outdated, and not very clean, with paper-thin walls and ceilings - we could clearly hear the guests upstairs late into the night and again early in the morning. There was no proper lobby or on-site staff, the AC created so much condensation that surfaces and even the TV were wet, and basic touches like coffee for the coffee maker were missing. While the beach was nearby, the..."
    Reviewed May 12, 2026
    Return • London (LHR) - Fort Myers (RSW)
    LHR - RSW • 2 stops RSW - LHR • 2 stops
    £1,781
    £1,407
    per traveller
    found 10 hours ago
    THE Palmview AND Sandpiper Inns
  • House (5 Bedrooms) | Interior
    Aug 2 - Aug 10

    Walk to Beach, Pool+hot Tub, Game Room Captiva 5bdr Coco Mango by Avantstay + Flight

    Captiva
    8 nights
    3.0 star property
    Return • London (LHR) - Fort Myers (RSW)
    LHR - RSW • 2 stops RSW - LHR • 2 stops
    Save 100% on your flight
    £5,459
    £3,897
    per traveller
    found 10 hours ago
    Walk to Beach, Pool+hot Tub, Game Room Captiva 5bdr Coco Mango by Avantstay
  • In-room safe, blackout curtains, iron/ironing board, cots/infant beds
    Aug 2 - Aug 10

    Casa Ybel Resort + Flight

    Mid Island
    8 nights
    2.5 star property
    8.8/10 - Excellent (351 reviews)
    "The beach view was very nice but during the entire time we were there people had to stay out of the water due to large amounts of seawood in the water and piled along the shore. The resort did nothing to try to clean up the beach.We drove up to Captiva and the water and beach were pristine. The girl at the front desk was totally uninterested when we checked in. Didn't explain anything about the resort. There was no information in the room about the restaurant, pool hours, how to call the front,..."
    Reviewed May 15, 2026
    Return • London (LHR) - Fort Myers (RSW)
    LHR - RSW • 2 stops RSW - LHR • 2 stops
    £2,234
    £1,685
    per traveller
    found 10 hours ago
    Casa Ybel Resort
  • 3 outdoor pools, pool cabanas (surcharge), pool umbrellas
    Aug 2 - Aug 10

    South Seas + Flight

    Captiva
    8 nights
    3.5 star property
    8.4/10 - Very good (1,003 reviews)
    "Their team was so helpful, friendly and kind. We had great experiences at all the venues and food options. Beautiful grounds, unlimited food, beach and pool options and a courteous team - home run!"
    Reviewed May 16, 2026
    Return • London (LHR) - Fort Myers (RSW)
    LHR - RSW • 2 stops RSW - LHR • 2 stops
    £2,477
    £1,889
    per traveller
    found 10 hours ago
    South Seas
  • On the beach, white sand, snorkelling, surfing
    Aug 2 - Aug 10

    Shalimar Beach Resort + Flight

    West End
    8 nights
    2.0 star property
    9.8/10 - Exceptional (52 reviews)
    Return • London (LHR) - Fort Myers (RSW)
    LHR - RSW • 2 stops RSW - LHR • 2 stops
    £2,108
    £1,663
    per traveller
    found 10 hours ago
    Shalimar Beach Resort

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
East Naples

East Naples

5/5(2 area reviews)

Beaches, shopping and restaurants are some highlights of East Naples. Make a stop by Gulf Shores Marina or Fifth Avenue South 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 £248 per night from 4 Jun to 5 Jun
£248
4 Jun - 5 Jun
includes taxes & fees
9/10 Wonderful! (1,791 reviews)
"Great place to stay for a long weekend getaway! Beautiful beach and the hotel and staff were very nice!"

Reviewed on 18 May 2026

Hilton Marco Island Beach Resort and Spa
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
The price is £182 per night from 20 May to 21 May
£182
20 May - 21 May
includes taxes & fees
9.4/10 Exceptional! (817 reviews)
"Great for kids!"

Reviewed on 18 May 2026

Great Wolf Lodge Naples
Fairways Inn of Naples

Fairways Inn of Naples

3 out of 5
103 Palm River Blvd Naples FL
Fully refundableReserve now, pay when you stay
The price is £67 per night from 2 Jun to 3 Jun
£67
2 Jun - 3 Jun
includes taxes & fees
9.4/10 Exceptional! (1,304 reviews)
"We loved we will definitely return"

Reviewed on 18 May 2026

Fairways Inn of Naples
See all 10,743 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 , 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

Fifth Avenue South

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
Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA

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
Naples Pier

Naples Pier

4.5/5(59 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

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

£39
per adult
94% of travellers recommend
Naples Sightseeing Boat Tour
Everglades National Park: Pontoon Boat Tour & Boardwalk

Everglades National Park: Pontoon Boat Tour & Boardwalk

£44
per adult
Everglades National Park: Pontoon Boat Tour & Boardwalk
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

£57
per adult
Naples: Sightseeing and Dining Cruises
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.