Old Naples Vacations from $905

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Your Old Naples Vacation

Book a customized vacation package to Old Naples and experience the wonders of this neighborhood from sunup to sundown. From its shopping and coastal beaches to its unique personality and vibe, there are lots of good reasons to visit Old Naples. When it's time to sightsee, you'll find a lot of popular attractions nearby including Naples Pier, Naples Zoo at Caribbean Gardens and Tin City. Visit one, two or all during your trip to Old Naples. Don't just think about it — turn it into reality! Lock in your ideal Old Naples vacation with Expedia and experience travel your way.

The Latest Old Naples Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
$905
per person
Dec 15 - Dec 20
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$1,348
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,182 reviews)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach
Save 100% on your flight
$3,122
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
Southseas

Southseas

Save 100% on your flight
$2,158
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Myers (RSW)
No reviews
Edison Beach House

Edison Beach House

$1,818
per person
Dec 26 - Jan 1
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,921 reviews)
Excellent

Reviewed on Oct 11, 2026

Where to stay in Old Naples

Find the best Old Naples areas and neighborhoods for the activities you enjoy most. Learn more about Old Naples
A person carrying a child on their shoulders on a bridge with a view of greenery and a clear sky.

Central Naples

If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing.

A wooden pier extending into calm waters at dusk, with two illuminated structures at the end.

East Naples

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.

A coastal landscape with a cruise ship, dense greenery, and a clear view of the ocean.

Naples Park

Located in North Naples, Naples Park is bounded by U.S. Route 41 and offers easy access to Vanderbilt Lagoon. Enjoy shopping at the nearby outdoor mall, The Mercato, for a delightful experience.

A sailboat with a blue canopy on calm waters, a red buoy, and a forested shoreline.

Vanderbilt Beach

1 out of top 10 points of interest in this area

While visiting Vanderbilt Beach, you might make a stop by sights like Vanderbilt Beach and Delnor-Wiggins Pass State Park.

A river with buildings on both sides, a clear sky, and a sunset.

Pelican Bay

The beaches and abundant dining options are top of the list for many visitors to Pelican Bay. A stop by Pelican Bay North Beach or Artis-Naples might round out your trip.

Old Naples Hotel Deals

Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL
Fully refundableReserve now, pay when you stay
$169 nightly
$188 total
Oct 30 - Oct 31
Total with taxes and fees
Hyatt House Naples/5th Avenue
Inn on Fifth

Inn on Fifth

699 5th Ave S Naples FL
Fully refundableReserve now, pay when you stay
$398 nightly
$442 total
Oct 28 - Oct 29
Total with taxes and fees
9.4/10 Exceptional! (1,004 reviews)
"Staff was very helpful and pleasant. We will be coming back for another stay soon. Blessings"

Reviewed on Oct 11, 2026

Inn on Fifth
Bellasera Resort

Bellasera Resort

221 9th St S Naples FL
Fully refundableReserve now, pay when you stay
$345 nightly
$383 total
Oct 18 - Oct 19
Total with taxes and fees
9.6/10 Exceptional! (2,340 reviews)
"Nice condo , very clean, a/c works great. Nice restaurant at the Claw Bar. Comfy bed , love the bath products. We were greeted with a bag of cookies in our room"

Reviewed on Oct 4, 2026

Bellasera Resort
See all 12,027 properties in Old Naples
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 Old Naples attractions

A bustling street with palm trees, a yellow building, and people walking.

Fifth Avenue South

9.4/10 (2,799 reviews)
Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.
See properties
A beach with people walking and a pier extending into the water.

Naples Pier

9.2/10 (4,448 reviews)
Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.
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A red barn with a blue door and a wooden staircase leading up to it.

Tin City

8.6/10 (2,742 reviews)
During your visit to Naples, you can do some window-shopping at Tin City. In the area, take in the entertainment choices and beautiful sunsets.
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A historic house with a green sign in front.

Naples Historical Society's Historic Palm Cottage

Delight in the informative tours, lush gardens and tangible history of this authentic piece of 19th-century Americana.
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Cambier Park

8.4/10 (18 reviews)
After visiting Cambier Park, make a plan to see the other sights and activities in Naples. Wander the beautiful beaches or discover the area's beautiful sunsets.
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Naples City Dock

9.6/10 (7 reviews)
Explore the waterfront of Naples City Dock and enjoy activities such as golfing in Naples. Wander the beautiful beaches or discover the area's beautiful sunsets.
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Norris Center

9.0/10 (4 reviews)
Enjoy a stop at Norris Center, an entertaining place to visit in Naples. Make time to visit the area's shops, or simply enjoy its top-notch restaurants.
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Port - O - Call Marina

Explore the waterfront of Port - O - Call Marina and enjoy activities such as golfing in Naples. Discover the area's beautiful sunsets and shops.
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Things to do

Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

$78
per adult
Naples: Sightseeing and Dining Cruises
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
Sunset Cruise Tour

Sunset Cruise Tour

$51
per adult
Sunset Cruise Tour
See all activities in 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.