Windstar on Naples Bay holiday lettings

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Why visit Windstar on Naples Bay

  • Spectacular waterfront views: Windstar on Naples Bay offers breathtaking vistas of the bay, perfect for enjoying serene sunsets.
  • Private beach access: Guests can indulge in the tranquillity of a private beach, ideal for sunbathing and relaxation.
  • Marine adventures: The marina provides opportunities for boating and water sports, catering to aquatic enthusiasts.
  • Charming community strolls: Explore picturesque streets and delightful neighbourhoods, making for leisurely afternoon walks.
  • Golfing at Windstar Golf Club: Enjoy a round of golf amidst beautiful scenery, perfect for both novice and experienced golfers.

Popular types of accommodation around Windstar on Naples Bay

Welcome to Windstar on Naples Bay, a serene retreat nestled in Naples, Florida. Here, you can choose from a variety of accommodation options, including condos, houses, and apartments. Enjoy direct access to a private beach and a water marina, perfect for boating enthusiasts. The clubhouse offers stunning waterfront views, while the Southpointe Yacht Club enhances your experience. Embrace the tranquillity and beauty of this picturesque community for an unforgettable getaway.

  • Condos: The most sought-after choice for holiday rentals in Windstar on Naples Bay, offering modern amenities and scenic views.
  • Houses: A popular alternative, these homes provide spacious living and a personal touch for your stay.
  • Apartments: Ideal for those seeking convenience and comfort, with easy access to local attractions.
  • Villas: Luxurious and spacious, perfect for a lavish getaway with family or friends.
  • Cottages: Charming and quaint, these provide a cozy retreat for a relaxing holiday experience.**

Top attractions near Windstar on Naples Bay

Windstar on Naples Bay in Naples, Florida, offers a delightful blend of outdoor experiences, culture, and picturesque views. Visitors can explore the beautiful beaches, enjoy leisurely strolls along charming streets, and take advantage of the marina for water activities. This vibrant community caters to families and solo travellers alike, providing ample opportunities for relaxation and exploration amidst the stunning natural surroundings of Naples Bay.

  • Fifth Avenue South: A vibrant street featuring upscale boutiques, art galleries, and fine dining options, ideal for a leisurely stroll and soaking in the local culture.
  • Naples Beach: A stunning stretch of white sand, perfect for sunbathing and swimming, where you can enjoy breathtaking sunsets and a relaxed beach atmosphere.
  • Naples Pier: A picturesque pier offering fishing, dolphin watching, and panoramic views of the Gulf, making it an excellent spot for excursions and photography.

Things to do recommended for couples

For a romantic getaway in Naples, explore the serene pathways of the Naples Botanical Garden or enjoy a sunset cruise on Naples Bay. Dine at a waterfront restaurant, savouring fresh seafood, or indulge in a couple's spa treatment at a local resort for a perfect day together.

Things to do recommended for families

Your family will delight in exploring the beautiful beaches of Naples, such as Vanderbilt Beach, or enjoy a fun-filled day at the Naples Zoo. Don't miss the chance to visit the interactive exhibits at the Golisano Children's Museum nearby for an engaging experience.

Things to do recommended for groups

Groups visiting Windstar on Naples Bay can indulge in a sunset cruise along the beautiful coastline, explore the vibrant local markets, and enjoy a guided nature tour in the nearby wetlands. Don't miss the chance to savour fresh seafood at charming waterfront restaurants.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Windstar on Naples Bay

If you're travelling with a group, family, or pets, or if you're seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windstar on Naples Bay with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space suitable for group gatherings. Thankfully, you can easily apply filters for all of these options, and much more, on Vrbo.
  • Traveling to Windstar on Naples Bay with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windstar on Naples Bay: For many families, a getaway wouldn’t feel complete without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Windstar on Naples Bay: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Windstar on Naples Bay

Windstar on Naples Bay offers an idyllic escape with its serene surroundings and stunning waterfront views. Explore the scenic Windstar Boulevard, indulge in a round at the Windstar Golf Club, or unwind at the Windstar Marina. This charming community provides a perfect blend of relaxation and recreation, making it ideal for families and couples alike. Experience the warm hospitality of Naples as you enjoy leisurely strolls and picturesque sunsets along the bay.

  • Naples: Naples is a vibrant city known for its stunning beaches and family-friendly atmosphere. Nestled along the Gulf of Mexico, it offers a plethora of outdoor experiences, from sunbathing on pristine shores to exploring local parks. Visitors will find an array of luxurious resorts and shopping centres, perfect for indulging in retail therapy or enjoying fine dining. Key attractions include the beautiful beaches and family-oriented theme parks, making it an ideal destination for those looking to relax and create lasting memories.
  • East Naples: East Naples is a charming neighbourhood that provides a delightful blend of outdoor activities and family enjoyment. Located close to Windstar on Naples Bay, it features several golf courses and parks that cater to both leisure and sporting enthusiasts. The area is also home to shopping malls and vibrant local markets, where visitors can discover unique merchandise and enjoy local cuisine. With its inviting atmosphere and proximity to beautiful beaches, East Naples is perfect for families seeking a fun-filled getaway.
  • Royal Harbor: Royal Harbor is a picturesque neighbourhood located a mere 1km from Windstar on Naples Bay. Known for its family-friendly vibe and coastal charm, it boasts beautiful beaches and scenic streets that invite leisurely strolls. The area offers a variety of shopping options and is popular for its golf facilities. With its close-knit community feel and convenient access to Naples' attractions, Royal Harbor is an excellent choice for those looking to immerse themselves in the local culture while enjoying a laid-back beach experience.

Best time to go to Windstar on Naples Bay

If you're planning a trip to Windstar on Naples Bay, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January65.7°F (18.7°C)No Rain (Dry)Mostly SunnyHighAverage
February68.2°F (20.1°C)No Rain (Dry)SunnyHighSlightly High
March70.3°F (21.3°C)No Rain (Dry)SunnyHighSlightly High
April75.4°F (24.1°C)No Rain (Dry)SunnyAverageAverage
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnyAverageAverage
July83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
August84.0°F (28.9°C)Light RainMostly SunnyLowSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnyLowSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnyLowSlightly Low
November73.0°F (22.8°C)No Rain (Dry)Mostly SunnyAverageAverage
December69.3°F (20.7°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that meets your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly area where you can initiate new trips, resume planning from where you last stopped, or manage your travel arrangements. Here, you’ll discover properties you’ve either saved or booked, neatly organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best holiday rentals near Windstar On Naples Bay?
The best holiday rentals near Windstar On Naples Bay are primarily located within East Naples, offering convenient access to the bay. You will find a wide selection here, including modern condos with views of the water and private holiday houses with ample space for relaxation. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties, but the best holiday rentals near Windstar On Naples Bay are often found closest to the water.

Many top-rated rentals feature amenities so you can have a comfortable stay, such as a refreshing pool for warm days, a spacious deck or patio for outdoor dining, and a blender for making cool drinks. These homes are ideal for families or groups seeking a relaxed coastal escape.
Are there any cheap holiday rentals near Windstar On Naples Bay?
There are several affordable holiday rentals near Windstar On Naples Bay, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around £100 per night. Some stays even drop below this price in September and June during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cosy studio apartments to modest family homes, providing a clean, comfortable base for your stay.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Windstar On Naples Bay while keeping costs down, so you can have a comfortable stay.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Windstar On Naples Bay?
There are over 300 pet-friendly holiday rentals near Windstar On Naples Bay, primarily found in the East Naples area. These properties, including private homes and condos, often come with amenities such as private decks, fully equipped kitchens, and Wi-Fi, ensuring a comfortable stay for both guests and their furry companions. Many offer easy outdoor access, which is ideal for pets.

To find the best pet-friendly holiday rentals near Windstar On Naples Bay, always verify specific house rules, pet size restrictions, and any additional fees directly with the property owner before making a reservation.
What are the top holiday rentals with pools near Windstar On Naples Bay?
There are over 770 holiday rentals near Windstar On Naples Bay that feature swimming pools. Guests can choose from a variety of options including private pools, often secured, ideal for families, and shared community pools. These properties are concentrated in East Naples and offer a range of amenities such as fully equipped kitchens, Wi-Fi, and spacious living areas, making them great for families and groups. The most common types of holiday rentals are condos and private holiday houses.

When selecting a property, consider whether a private pool, offering seclusion, or a shared pool, which often includes access to additional facilities like hot tubs or fitness centres, better suits your needs. Many pools are heated, providing comfort during cooler months, and outdoor pools are popular for enjoying the Florida sunshine.
What are the best family holiday rentals near Windstar On Naples Bay?
There are over 570 family-friendly holiday rentals located near Windstar On Naples Bay, primarily consisting of private homes and condos, offering ample space and comfort for groups. These properties often boast multiple bedrooms and bathrooms, full kitchens for meal preparation, and essential amenities like washer/dryers. Many also feature outdoor play areas such as patios, yards, or gardens, and some even include playgrounds or pools, along with entertainment options like books, games, and video games.

When selecting a holiday rental for your family, look for properties that provide separate spaces for adults and children to relax, and prioritise those with practical utilities like laundry facilities to simplify your stay. Many homes offer child-specific amenities such as travel cribs, highchairs, and stair gates. Staying close to Windstar On Naples Bay means less travel time and more opportunities to enjoy your chosen activities.
Are there any luxury holiday rentals near Windstar On Naples Bay?
Near Windstar On Naples Bay, guests can find several luxury holiday rentals that offer natural scenery with modern comfort. These properties often feature amenities such as private heated pools, spa-style bathrooms with designer toiletries, gourmet kitchens, and stunning lake views. Many homes also include a private chef service, executive rooms, and premium bedding with Egyptian cotton sheets.

These homes are ideal for families or larger groups, providing conveniences like climate control cooling and a comfortable stay. Many of these top-tier stays are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a holiday rental near Windstar On Naples Bay?
Holiday rentals near Windstar On Naples Bay offer a wide range of options suitable for different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around £100 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around £245 per night, offering more comfort and privacy. Upscale options can cost £345 or more per night, especially for properties with premium amenities or desirable locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Windstar On Naples Bay?
When visiting Windstar On Naples Bay, several excellent areas offer holiday rentals to enhance your stay.

East Naples is a superb choice, providing convenient access to Windstar On Naples Bay and a range of local amenities. Properties here often feature beautiful views and are well-suited for those seeking a tranquil yet accessible location.

For guests who appreciate being closer to a broader selection of dining and shopping, the areas around US-41 (Tamiami Trail East) are highly recommended. These properties are a short drive from Windstar On Naples Bay, offering convenient access to local attractions and the vibrant coastal lifestyle.
What is the cheapest month to stay near Windstar On Naples Bay?
The cheapest time to find holiday rentals near Windstar On Naples Bay is typically during the late Spring (June) and early Autumn (September). September is frequently the single cheapest month to stay, often offering various savings on properties. Guests can often find lower rates during these months, along with greater availability for holiday rentals.
Are there any lakefront holiday rentals near Windstar On Naples Bay
Lakefront holiday rentals near Windstar On Naples Bay are predominantly found along the freshwater lakes and canals that are part of the extensive water systems in the Naples area. These properties are a short drive from Windstar On Naples Bay, offering convenient access to water activities such as kayaking, fishing, paddleboating, or simply relaxing by the shore.

These homes often feature spacious decks, private boat docks, and full kitchens, making them ideal for families and larger groups. Guests can enjoy lake views, spot local wildlife, and unwind in peaceful surroundings.
Are there any top beachfront holiday rentals near Windstar On Naples Bay
Beachfront holiday rentals near Windstar On Naples Bay are primarily found along the Gulf of Mexico coastline, offering direct access to the sand. Many properties boast ocean-view balconies or are just steps from the water. While Windstar On Naples Bay itself is on the bay, guests seeking beachfront properties will find options along Gulf Shore Boulevard North or further north towards Vanderbilt Beach, providing a mix of lively dining and shopping within walking distance, alongside quieter spots for relaxation.

These properties often provide beach chairs, umbrellas, and offer oceanfront pools, making for a convenient stay. Accommodation types range from ocean-facing rooms and suites with private terraces to multi-bedroom units with extra living space, suitable for various guests.
Are there any monthly holiday rentals near Windstar On Naples Bay?
Vrbo offers excellent options for monthly holiday rentals near Windstar On Naples Bay, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer holiday with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Windstar On Naples Bay.
Are there any last-minute holiday rentals near Windstar On Naples Bay?
Vrbo makes it simple to find last-minute holiday rentals near Windstar On Naples Bay that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.

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