South Naples Mountain Vacations 2026/2027

Plan, book, travel with confidence
Better together
Save up to $2,000 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
Plan, book, and manage your trip all in one place

Top Mountain vacation packages in South Naples

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

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$558

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (108 reviews)

Beautiful resort.. all of the food from by the pool, to the dining hall, to the higher end are all incredible- the only down side is the food is pricey.

Reviewed on Sep 17, 2026

The Perry Hotel Naples

Save 100% on your flight

$1,402

per person

Dec 7 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$682

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,012 reviews)

Loved the lazy river, staff was pleasant and helpful, and we loved our 1-bedroom villa.

Reviewed on Sep 15, 2026

Shell Island Beach Club

East End

Save 100% on your flight

$1,267

per person

Nov 28 - Dec 5

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (25 reviews)

This well-equipped apartment overlooks the grounds and swimming pool with views of the beach just yards away. Fully restored after the devastation from hurricane Ian 4 years ago it’s in great shape and we had a wonderful stay. The staff work tirelessly to keep the place as it should be and nothing was too much trouble. I can’t recommend it highly enough.

Reviewed on Sep 6, 2026

Innovation Hotel

Save 100% on your flight

$684

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.8/10 Exceptional! (649 reviews)

We were there for a girl's weekend. The hotel is beautiful and customer service amazing. We had breakfast both mornings and ate at the bar one afternoon. Our experience was nothing short of perfect. I look forward to returning!

Reviewed on Sep 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to South Naples

View all trips

5* Mountain vacations in South Naples

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

Sundial Beach Resort & Spa

Mid Island

Save 100% on your flight

$1,002

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Sundial Resort is the best place to stay on Sanibel! We have been there numerous times, and also stayed in other resorts and condos on Sanibel and Captive, but Sundial has the best vibe, family entertainment and great food!

Reviewed on Sep 15, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,719

per person

Dec 1 - Dec 5

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

The Ritz-Carlton Naples, Tiburón

$2,125

per person

Nov 10 - Nov 15

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (681 reviews)

Don't see what you're looking for?

See all available trips from Columbus to South Naples

View all trips

3 Night Mountain vacations in South Naples

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

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

$495

per person

Oct 18 - Oct 21

found 7 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.4/10 Exceptional! (108 reviews)

Beautiful resort.. all of the food from by the pool, to the dining hall, to the higher end are all incredible- the only down side is the food is pricey.

Reviewed on Sep 17, 2026

The Perry Hotel Naples

Save 100% on your flight

$918

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Inn at Pelican Bay

Pelican Bay

$610

per person

Oct 31 - Nov 3

found 16 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,004 reviews)

Pianist, shuttle, staff

Reviewed on Sep 17, 2026

Don't see what you're looking for?

See all available trips from Columbus to South Naples

View all trips

4 Night Mountain vacations in South Naples

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

The Bay Inn at Lani Kai

$502

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

7.8/10 Good! (502 reviews)

This town is awesome

Reviewed on Sep 14, 2026

The Perry Hotel Naples

Save 100% on your flight

$712

per person

Dec 1 - Dec 5

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Tween Waters Island Resort & Spa

Save 100% on your flight

$607

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Great place to relax and enjoy some R&R

Reviewed on Sep 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to South Naples

View all trips

How to plan for a mountain vacation in South Naples?

The first step to planning your mountain vacation to South Naples is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near South Naples, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in South Naples, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your South Naples mountain vacation.

What amenities should I look for when booking a mountain resort in South Naples?

When booking accommodation for your mountain vacation to South Naples, check to see if where you're staying has heating. South Naples's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your South Naples vacation package.

Why should I choose a package for my mountain vacation in South Naples?

Choosing a package for your South Naples vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2026 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment.

What does a South Naples package typically include?

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to South Naples from $495. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each South Naples vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking South Naples all-inclusive vacation packages as these include all meals.

How can I book my South Naples on Expedia?

Comparing some of the best deals using the search wizard is one of the first steps to booking your South Naples mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your South Naples package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's payment plans.

Why book your South Naples mountain vacation with Expedia?

With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your South Naples vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts.

Can I cancel my mountain vacation package booking?

Yes, as most of Expedia's mountain vacation packages to South Naples are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all South Naples vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible South Naples vacation packages.

What types of mountain accommodations are available in South Naples?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to South Naples. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.