South Naples Mountain Vacations and Getaways

Book a Mountain Hotel + Flight or Car together to unlock savings

  • 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.
Landing Fort Myers - Eastwood Village

Landing Fort Myers - Eastwood Village

Eastwood Village
Save 100% on your flight
$633
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
10/10 Exceptional! (2 reviews)
Nice place

Reviewed on Mar 25, 2026

The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$841
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (970 reviews)
Front desk staff-awesome Valet staff- great Roof top manager and waitress. RUDE. Everyone else was terrific and property was clean, etc.

Reviewed on Aug 7, 2026

Shell Island Beach Club

Shell Island Beach Club

East End
Save 100% on your flight
$993
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
9.6/10 Exceptional! (24 reviews)
Great place to stay on the beach! Woman at the front desk was rude!

Reviewed on Jun 7, 2026

Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

Save 100% on your flight
$941
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (7 reviews)
Close by beach and 5th avenue

Reviewed on Jul 10, 2026

Wiggins Pass Chalet

Wiggins Pass Chalet

Save 100% on your flight
$689
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (281 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.
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$428
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.6/10 Exceptional! (970 reviews)
Front desk staff-awesome Valet staff- great Roof top manager and waitress. RUDE. Everyone else was terrific and property was clean, etc.

Reviewed on Aug 7, 2026

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

$442
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (22 reviews)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
$591
per person
Oct 15 - Oct 18
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,015 reviews)
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 Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$770
per person
Oct 22 - Oct 26
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (970 reviews)
Front desk staff-awesome Valet staff- great Roof top manager and waitress. RUDE. Everyone else was terrific and property was clean, etc.

Reviewed on Aug 7, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

$821
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
Everything excellent Excellent

Reviewed on Aug 7, 2026

Bellasera Resort

Bellasera Resort

Old Naples
Save 100% on your flight
$948
per person
Oct 22 - Oct 26
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,307 reviews)
Don't see what you're looking for?
See all available trips from Columbus to South Naples
View all trips

Find amazing mountains vacations in South Naples

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 $428. 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.

Things to do

Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

$66
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

$57
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

$78
per adult
Naples: Sightseeing and Dining Cruises
See all activities in South Naples

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.