South Naples Vacation Packages 2026 from $711

South Naples flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Tween Waters Island Resort & Spa

Save 100% on your flight

$711

per person

Dec 10 - Dec 15

found 6 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free resort features a private beach, a full-service spa, and a marina. Family-friendly amenities include a children's pool and kid-friendly dining, along with kayaking. Free self parking is free for guests, and you can enjoy a meal in one of the 3 restaurants.

Olde Marco Island Inn and Suites

Olde Marco

Save 100% on your flight

$909

per person

Dec 17 - Dec 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free hotel features 4 restaurants, a bar/lounge, and an outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.

Landing Furnished Apartments minutes from Downtown Fort Myers

Hancock

Save 100% on your flight

$1,273

per person

Dec 21 - Dec 28

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This apartment features a gym and a seasonal outdoor pool. WiFi in public areas is free. A virtual front desk are provided for your convenience.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,619

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

Windward Passage Resort

Save 100% on your flight

$803

per person

Dec 15 - Dec 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. Laundry facilities are provided for your convenience.

Top South Naples hotels deals

Staybridge Suites Naples – Marco Island by IHG

9401 Triangle Blvd Naples FL

Free Cancellation

$125 nightly

$139 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Conty's Motel

11238 Tamiami Trail East Naples FL

$65 nightly

$72 total

Sep 30 - Oct 1

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's an outdoor pool on site, and a terrace and a garden are also provided.

Pool

Pet friendly

GreenLinks Golf Villas at Lely Resort

7995 Mahogany Run Lane Naples FL

Get rates

This smoke-free aparthotel features a golf course, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking. You'll appreciate the gym, bar/lounge, and barbecue grills.

Pool

Hot Tub

Holiday Inn Express Naples South I-75 by IHG

3837 Tollgate Blvd Naples FL

Free Cancellation

$88 nightly

$98 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

La Quinta Inn & Suites by Wyndham Naples East (I-75)

185 Bedzel Cir Naples FL

Free Cancellation

Reserve now, pay when you stay

$73 nightly

$81 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features an outdoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Fairfield Inn & Suites by Marriott Naples

3808 White Lake Blvd Naples FL

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$109 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

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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.

Stay near popular South Naples attractions

Flamingo Island Course - Lely Resort

8.8/10 (6 reviews)

Enjoy a round of golf in Naples at Flamingo Island Course - Lely Resort. Wander the beautiful beaches and seaside in the area.

See properties

Frequently asked questions

How much are vacation packages to South Naples?

With Travelocity vacation packages, you can live it up in South Naples for as low as $711. Hotels, flights and adventures — we're a one-stop shop for all of them. You'll save tons just by combining your bookings together. And with all that taken care of before you leave, you don't have to worry about a thing.

Where can I get the best vacation package deals for South Naples?

Book your dream vacation with Travelocity. With access to 400 airlines and at least 1,000,000 hotels around the world, finding the perfect South Naples package deal couldn't be easier.

Why should I book my South Naples vacation bundle via Travelocity?

Because you'll never wander alone if you lock in your trip with us, and we offer 24/7 customer support and exceptional service to boot. Add to that our Price Match Guarantee and a massive range of destinations to choose from. It's our job to make your vacation as unforgettable as possible.

Can I save money on my South Naples car rental if I bundle it with my hotel or flight?

You most certainly can — and booking one of our South Naples vacation packages is the best way to do this. Bundle any combination of a hotel, flight, car and experience and score great discounts. The more you book, the more you'll save. There are so many top attractions around South Naples to put on your must-see list, including PortMiami (100 mi from South Naples). Nothing tops exploring thrilling places like this with the freedom of your own wheels.

What is the best time of year to go to South Naples?

January, February and May is high season here, while August, October and December are more quiet. If your bank balance is your primary consideration, try to avoid visiting during as it's usually the dearest time. The least expensive month to visit is .