A wooden boardwalk surrounded by palm trees and lush greenery.

South Naples Vacations from $636

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The Latest South Naples Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 19 - Dec 23

    Marriott Sanibel Harbour Resort & Spa + Flight

    Punta Rassa
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,003 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $893
    $636
    per traveler
    found 1 day ago
    Marriott Sanibel Harbour Resort & Spa
  • Jan 10 - Jan 14

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,001 reviews)
    "Overall, worth the stay. The place could use some updates."
    Reviewed November 5, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop PGD - PSM • Nonstop
    Save 100% on your flight
    $2,972
    $1,919
    per traveler
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • Jan 10 - Jan 14

    The Perry Hotel Naples + Flight

    Naples
    4 nights
    4.5 star property
    9.6/10 - Exceptional (1,256 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop PGD - PSM • Nonstop
    Save 100% on your flight
    $1,494
    $979
    per traveler
    found 1 day ago
    The Perry Hotel Naples
  • Jan 14 - Jan 18

    Spacious Family Retreat Port Charlotte + Flight

    Port Charlotte
    4 nights
    2.0 star property
    10/10 - Exceptional (4 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop RSW - BOS • 1 stop
    $2,651
    $1,820
    per traveler
    found 1 day ago
    Spacious Family Retreat Port Charlotte
  • Jan 14 - Jan 19

    A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave + Flight

    Naples
    5 nights
    3.0 star property
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop RSW - BOS • 1 stop
    Save 100% on your flight
    $3,197
    $2,279
    per traveler
    found 1 day ago
    A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave

Discover the most popular places to visit in South Naples

South Naples Hotel Deals

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.

Frequently Asked Questions

What's included in a South Naples vacation package?

A South Naples vacation package in Lely lets you combine flights, hotel stays, and rental cars. Travelers typically fly into Southwest Florida International Airport (RSW) when visiting the area. Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a South Naples vacation package?

When you bundle, you can save up to 30%*. To save money on a South Naples package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What is the best time to visit South Naples?

The best time for a South Naples vacation package in Lely is typically from January through March, which is the peak season for demand. During this period, you might also catch events like 'Never Stop Believin' and Kam Falk' in February. Timing reflects Lely specifically, so conditions may differ elsewhere in the region.

Which destinations should I consider for a South Naples vacation?

For a South Naples vacation, choosing the right base depends on your travel style. The region's primary lodging options are concentrated in one area:

  • Lely: This area is a strong choice for a beach, outdoor, or family-friendly South Naples vacation, offering plenty of lodging choices and access to various activities.

Is South Naples better suited for a beach vacation or a cultural trip?

South Naples is primarily a beach destination, known for its beautiful coastline and abundant outdoor activities. Travelers can enjoy the white sands and Gulf waters at places like Naples Beach and Marco Beach, making it an ideal choice for a South Naples vacation focused on sun and sand.


While beaches are a major draw, South Naples also offers urban attractions. Areas like Fifth Avenue South provide opportunities for shopping and dining, catering to those who appreciate city amenities alongside their beach experience. Your South Naples vacation package can be tailored to combine both relaxation and urban exploration.

Which airport should I use for a South Naples vacation?

For a South Naples vacation, several airports serve the region. Miami International Airport (MIA) offers a wide range of connections, while Southwest Florida International Airport (RSW) in Fort Myers is another major gateway. For closer access, consider Naples Municipal Airport (APF). All provide onward travel to your South Naples destination.

What are the top things to do in South Naples?

A South Naples vacation is easiest to explore from a base like Lely, which offers access to a variety of attractions:


Browse and book things to do in South Naples on Expedia.

Can I change or cancel my South Naples vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking South Naples vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later South Naples vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your South Naples vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to South Naples?

To find last-minute vacation packages to South Naples, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on South Naples vacation packages?

Free cancellation on a South Naples vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a South Naples vacation as a package or separately?

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your South Naples getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my South Naples vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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