Winter Vacation Rentals & Cabin Rentals in Naples, FL

Compare 10,784 available beachfront holiday vacation home properties, starts from $14

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ACCOMMODATION TYPES

Monthly & Short Term Winter Vacation Rentals in Naples, FL: Top Deals

Greenlinks Lake View Condo
Greenlinks Lake View Condo
Greenlinks Lake View Condo
Greenlinks Lake View Condo
Greenlinks Lake View Condo
Greenlinks Lake View Condo
Greenlinks Lake View Condo
4.7 (7 reviews)
Greenlinks Lake View Condo
Condo
$100 /night
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Bayfront Inn 5th Avenue
Bayfront Inn 5th Avenue
Bayfront Inn 5th Avenue
Bayfront Inn 5th Avenue
Bayfront Inn 5th Avenue
Bayfront Inn 5th Avenue
Bayfront Inn 5th Avenue
4.0 (258 reviews)
Bayfront Inn 5th Avenue
Hotel
$125 /night
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Bologna Golf Condo in the Lely Resort
Bologna Golf Condo in the Lely Resort
Bologna Golf Condo in the Lely Resort
Bologna Golf Condo in the Lely Resort
Bologna Golf Condo in the Lely Resort
Bologna Golf Condo in the Lely Resort
Bologna Golf Condo in the Lely Resort
4.5 (3 reviews)
Bologna Golf Condo in the Lely Resort
Resort
$152 /night
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Ramada by Wyndham Naples
Ramada by Wyndham Naples
Ramada by Wyndham Naples
Ramada by Wyndham Naples
Ramada by Wyndham Naples
Ramada by Wyndham Naples
Ramada by Wyndham Naples
4.0 (3127 reviews)
Ramada by Wyndham Naples
Hotel
$88 /night
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Le Monaco Condo at Olde Naples
Le Monaco Condo at Olde Naples
Le Monaco Condo at Olde Naples
Le Monaco Condo at Olde Naples
Le Monaco Condo at Olde Naples
Le Monaco Condo at Olde Naples
Le Monaco Condo at Olde Naples
4.6 (4 reviews)
Le Monaco Condo at Olde Naples
Condo
$120 /night
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FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
4.5 (11 reviews)
FACILITIES ARE OPEN "POOL, BEACHES & RESTAURANTS" ENJOY THE ASIAGO CONDO
Condo · 6 Guests · 2 Bedrooms
$81 /night*
View deal
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
Hyatt House Naples/5th Avenue
4.2 (869 reviews)
Hyatt House Naples/5th Avenue
House
$127 /night
View deal
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
4.7 (31 reviews)
Modern Solterra Condo with Community Pool and Hot Tub at Lely Resort
Condo · 8 Guests · 3 Bedrooms
$117 /night*
View deal
Trianon Old Naples
Trianon Old Naples
Trianon Old Naples
Trianon Old Naples
Trianon Old Naples
Trianon Old Naples
Trianon Old Naples
4.4 (935 reviews)
Trianon Old Naples
Hotel
$119 /night
View deal
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Similar Inspirational Vacation Rental Destinations

Which Price Range Is Considered As A Good Deal in Naples, FL Area?
Vacation Condo & House Rental Price Information in Naples, FL
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The graph shows the percentages of vacation homes in each price bucket. Naples has the largest percentage (29.81%) of homes in $100 - $150 price range.
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What are some great activities, communities or places of interest for snowbirds in Naples, FL?
Best Places for Snowbirds to Visit in Naples, FL
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Naples, FL is a perfect destination for snowbirds looking to enjoy the warm weather and sunny beaches. With its close proximity to numerous healthcare facilities, it's easy to find the medical attention one needs here. Additionally, there are plenty of outdoor activities like golfing, fishing, and kayaking that make Naples a great spot for seniors who want to explore and stay active. Here are some of the best places for snowbirds to visit in Naples:

  • Naples Zoo at Caribbean Gardens

    This zoo offers over 900 animals from around the world, including African lions and Florida panthers. The zoo also has several attractions such as an African elephant exhibit and a children’s play area, making it a great family-friendly activity for snowbirds.

  • Delnor-Wiggins Pass State Park

    This state park offers a wide array of recreational activities, including swimming, fishing, boating, and biking. There’s also a beach with white sand and crystal clear waters, making it ideal for snowbirds looking to relax and soak up the sun.

  • The Village on Venetian Bay

    The Village on Venetian Bay is a waterfront shopping center with dozens of stores, restaurants, and entertainment venues. The views of the Gulf of Mexico are unbeatable, and the shops offer everything from luxury items to local souvenirs.

How Many Rental Accommodations Are Pets Friendly in Naples, FL?
Pets Allowed vs Not Allowed in Naples, FL
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13.15% of vacation homes in Naples are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
What Are The Must-Visit Places in Naples, FL?
Destinations To Visit During the Winter in Naples, FL
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How Many Airports in Naples, FL?
Top Airports in Naples, FL
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Here are the airports that located near Naples:

Other Vacation Rentals Ideas

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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