South Naples Mountain Vacations and Getaways

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

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
$596
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip 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
$782
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
Excelente estadía en The Perry Hotel Naples. El hotel es moderno, hermoso y muy bien cuidado, con un ambiente tranquilo y relajante. La atención del personal fue excelente y disfrutamos mucho las instalaciones y la ubicación. Definitivamente un lugar al que volveríamos y que recomendamos para una escapada en Naples.

Reviewed on Sep 13, 2026

Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

Daniels Corridor
Save 100% on your flight
$671
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (14 reviews)
Very Clean

Reviewed on Sep 9, 2026

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
Save 100% on your flight
$987
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Very clean resort; nice that beach chairs and umbrella available; good location

Reviewed on Sep 14, 2026

Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

Save 100% on your flight
$1,264
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.6/10 Exceptional! (11 reviews)
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5* Mountain vacations in South Naples

Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton Naples, Tiburón

The Ritz-Carlton Naples, Tiburón

$860
per person
Oct 30 - Nov 1
found 8 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
9.2/10 Wonderful! (681 reviews)
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
$2,090
per person
Nov 21 - Nov 28
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (2,690 reviews)
We booked with a 3rd party , the web pics showed a balcony. Are room had now balcony. Went to Terry Manager was accommodating although he stated the pics from a 3rd party was on 3rd party web not on the resorts web. Needless to say every was very clean the tiki bar staff very sweet. Be warned iof the sand flees u can not see them and they will eat u alive

Reviewed on Sep 12, 2026

Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
Save 100% on your flight
$2,960
per person
Nov 22 - Nov 26
just found
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (34 reviews)
Outstanding massage

Reviewed on Sep 1, 2026

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3 Night Mountain vacations in South Naples

Price found within the past 48 hours. Click for updated prices.
Landing Apartments Fort Myers near Olympia Pointe

Landing Apartments Fort Myers near Olympia Pointe

$381
per person
Dec 5 - Dec 8
found 9 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
8.8/10 Excellent! (9 reviews)
Great pool,comfortable room.

Reviewed on Mar 27, 2026

The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$916
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)
Excelente estadía en The Perry Hotel Naples. El hotel es moderno, hermoso y muy bien cuidado, con un ambiente tranquilo y relajante. La atención del personal fue excelente y disfrutamos mucho las instalaciones y la ubicación. Definitivamente un lugar al que volveríamos y que recomendamos para una escapada en Naples.

Reviewed on Sep 13, 2026

Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

Daniels Corridor
$450
per person
Dec 5 - Dec 8
found 13 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
9.2/10 Wonderful! (14 reviews)
Very Clean

Reviewed on Sep 9, 2026

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4 Night Mountain vacations in South Naples

Price found within the past 48 hours. Click for updated prices.
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

South Island
$607
per person
Nov 17 - Nov 21
just found
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (13 reviews)
Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$782
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
Excelente estadía en The Perry Hotel Naples. El hotel es moderno, hermoso y muy bien cuidado, con un ambiente tranquilo y relajante. La atención del personal fue excelente y disfrutamos mucho las instalaciones y la ubicación. Definitivamente un lugar al que volveríamos y que recomendamos para una escapada en Naples.

Reviewed on Sep 13, 2026

Casa Ybel Resort

Casa Ybel Resort

Mid Island
Save 100% on your flight
$615
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
8.8/10 Excellent! (417 reviews)
Comfortable accommodations Friendly staff Nice poolside lunch service. Beach is much more shell crushed than in the past and difficult to walk on without sand shoes.

Reviewed on Sep 13, 2026

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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 $381. 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

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

$67
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

$73
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

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

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