Wing South Vacations from $334

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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.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $891, price is now $334 per person
$334
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
The staff-Erika and Penny, were so wonderful and attentive to our requests! The clean room, the beautiful grounds and the restaurant manager, Raymond, so friendly. Just a perfect stay and memories made. Thank you. Catherine & Ernie K

Reviewed on Nov 28, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was $751, price is now $342 per person
$342
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
In general, excellent service.

Reviewed on Nov 30, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,450, price is now $708 per person
$708
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
Yes wonderful stay as usual !!!!

Reviewed on Dec 1, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Price was $1,443, price is now $743 per person
$743
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
El personal súper amable y todo muy limpio,la habitación excelente

Reviewed on Nov 24, 2025

Wiggins Pass Chalet

Wiggins Pass Chalet

4 out of 5
Save 100% on your flight
Price was $1,078, price is now $612 per person
$612
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (236 reviews)
Clean and comfortable

Reviewed on Nov 23, 2025

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
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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
$244 nightly
The price is $271 total per night from Dec 14 to Dec 15
$271 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,950 reviews)
Great !

Reviewed on Nov 30, 2025

Naples Grande Beach Resort
Inn on Fifth

Inn on Fifth

4 out of 5
699 5th Ave S Naples FL
Fully refundable
$311 nightly
The price is $346 total per night from Dec 14 to Dec 15
$346 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
Nice hotel , close to everything

Reviewed on Nov 29, 2025

Inn on Fifth
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
$275 nightly
The price is $305 total per night from Dec 12 to Dec 13
$305 total
Dec 12 - Dec 13
Total with taxes and fees
8.8/10 Excellent! (1,660 reviews)
The service was great...staff was polite and helpful, accessibility to beach and pool was convenient, towel check-out was smooth and organized, and breakfast buffet was fantastic.

Reviewed on Nov 27, 2025

Hilton Marco Island Beach Resort and Spa
See all 10,934 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
Vanderbilt Beach

Vanderbilt Beach

If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.

Vanderbilt 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

Things to do

Sunset Tour in Naples Bay on a New Godfrey- All included

Sunset Tour in Naples Bay on a New Godfrey- All included

$110
per adult
100% of travellers recommend
Sunset Tour in Naples Bay on a New Godfrey- All included
Wild Dolphin Boat Tour

Best of Marco Dolphin Tour

$100
per adult
Best of Marco Dolphin Tour
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

$127
per adult
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco 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.