Windemere holiday lettings

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Why visit Windemere

  • Stunning Beaches: Windemere boasts beautiful beaches, particularly Perdido Beach, perfect for sunbathing and water sports.
  • Outdoor Adventures: Explore nearby national parks and islands, offering a variety of thrilling activities amidst nature.
  • Family-Friendly Atmosphere: The area is welcoming to families, with plenty of activities to engage visitors of all ages.
  • Diverse Accommodation Options: Choose from charming cottages, modern condos, or beachfront rentals for a perfect stay.
  • Delightful Dining: Enjoy a range of dining options that showcase local flavours and enhance your holiday experience.

Popular types of accommodation around Windemere

You've chosen to visit Windemere, and now the exciting task of selecting your accommodation begins. Explore the diverse options available, from charming cottages to modern houses. For those seeking the convenience of a communal lifestyle, Windemere condos and condominiums offer a fantastic choice. Don’t forget to check out the stunning beachfront rentals for a picturesque stay. Your perfect getaway awaits in this beautiful destination!

  • Condos: The top choice for visitors in Windemere, offering modern amenities and easy beach access.
  • Houses: A popular option for families or groups seeking space and privacy during their stay.
  • Cottages: These charming retreats provide a quaint and cosy atmosphere, perfect for a romantic escape.
  • Apartments: Conveniently located and well-equipped, ideal for short stays or simple getaways.
  • Villas: Luxurious and spacious, perfect for those looking for a high-end experience in Windemere.**

Top attractions near Windemere

Windemere, located in Perdido Key, Florida, offers a delightful mix of outdoor adventures and beach experiences. Visitors can explore stunning beaches, national parks, and nearby islands, perfect for those seeking relaxation or thrilling activities. A must-visit is Perdido Beach, where you can soak up the sun or engage in water sports. Whether you're travelling solo, as a family, or with friends, Windemere provides a charming escape filled with natural beauty and exciting attractions.

  • Perdido Key Beach: A stunning stretch of sandy shoreline, perfect for sunbathing and swimming. This beach boasts a relaxed atmosphere with picturesque views and is ideal for a peaceful day by the sea.
  • Ono Island: A hidden gem offering a blend of outdoor activities and beach vibes. Explore its serene environment, perfect for kayaking, fishing, or simply enjoying the natural beauty.
  • Perdido Key State Park: An adventure seeker’s paradise with scenic trails, picnic spots, and pristine beaches. Experience hiking, wildlife viewing, and breathtaking coastal scenery.

Things to do recommended for couples

Enjoy a romantic getaway in Windemere, Perdido Key. Take a sunset stroll along the pristine beach, indulge in a candlelit dinner at a waterfront restaurant, or explore the scenic nature trails hand in hand, creating unforgettable memories together amidst the stunning coastal landscape.

Things to do recommended for families

Your family will have a fantastic time in Windemere, exploring Adventure Island for thrilling arcade games, enjoying sports at the Orange Beach Sportsplex, and having fun at Arena The Next Level, all within a short drive. These activities promise excitement and family bonding moments.

Things to do recommended for groups

Enjoy a round of golf at Lost Key Golf Club, just 1.6km from Windemere, or shop together at the Tanger Outlet Center, 9.3km away. For outdoor adventure, hike the scenic trails at Cotton Bayou Trailhead, located 5.0km from your base.

What do I need to keep in mind when booking a vacation around Windemere

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

  • Traveling to Windemere with a group: Think about how many bedrooms you'll require, along with amenities like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can refine your search for all of these options and more on Vrbo.
  • Traveling to Windemere with young kids: Travelling with young children can present its challenges. It is 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 Windemere: For many, a family holiday isn’t truly complete without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Windemere: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Windemere

Windermere and nearby Perdido Key offer a charming escape with a family-friendly atmosphere and welcoming locals. Visitors can explore the stunning beaches of Perdido Key, bask in the sun, and indulge in water sports. The area boasts beautiful landscapes and a relaxed vibe, making it an ideal spot for a tranquil getaway. Enjoy delightful dining options and local attractions that promise to enhance your holiday experience in this picturesque part of Florida.

  • Orange Beach: Situated a mere 5.6km from Windemere, Orange Beach is a vibrant city that offers a delightful blend of beachside relaxation and urban excitement. Visitors flock to this coastal haven for its stunning white sandy beaches and a plethora of outdoor activities. Here, you can shop at local centres, unwind at luxurious resorts, or hit the golf courses that dot the area. The local landmarks, such as the family-friendly beach and charming town neighbourhood, provide a perfect backdrop for a memorable holiday experience.
  • Perdido Key: Located just 621m from Windemere, Perdido Key is a quaint village known for its picturesque beaches and outdoor pursuits. This idyllic spot is perfect for those seeking a laid-back atmosphere with easy access to shopping centres and renowned golf courses. With its stunning coastline and family-oriented beaches, Perdido Key serves as a fantastic destination for relaxation and exploration, allowing visitors to soak up the sun while enjoying the vibrant community feel.
  • Holiday Harbor: Just 621m away from Windemere, Holiday Harbor offers a charming neighbourhood experience that is perfect for families and outdoor enthusiasts alike. The area features recreational spaces and shopping centres, making it a convenient spot for all your holiday needs. With easy access to beautiful beaches and family-friendly attractions, Holiday Harbor is an ideal location for those looking to enjoy a serene escape while still being close to the action.

Best time to go to Windemere

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January52.7°F (11.5°C)Light RainMostly SunnyLowModerately Low
February56.8°F (13.8°C)Light RainMostly SunnyAverageModerately Low
March62.4°F (16.900000000000002°C)Light RainMostly SunnyAverageAverage
April68.0°F (20.0°C)Light RainMostly SunnyAverageAverage
May75.0°F (23.9°C)Light RainMostly SunnyHighModerately High
June81.3°F (27.4°C)Light RainMostly SunnyHighModerately High
July82.6°F (28.1°C)Light RainMostly SunnyHighModerately High
August82.8°F (28.200000000000003°C)Moderate RainMostly SunnyAverageAverage
September79.2°F (26.200000000000003°C)Light RainMostly SunnyAverageAverage
October70.9°F (21.6°C)Light RainSunnyAverageAverage
November60.8°F (16.0°C)Light RainMostly SunnyLowAverage
December56.7°F (13.7°C)Light RainMostly SunnyLowModerately Low

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? It might be worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo accommodation that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, and manage your travel arrangements with ease. You can conveniently access properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore the 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 Windemere?
The best holiday rentals near Windemere are primarily found directly in Perdido Key, Florida, offering convenience and stunning coastal access. You will find a great selection of properties, with the majority being stylish condos and also many spacious private holiday houses, great for those seeking a beachfront experience. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. Many guests look for the best holiday rentals near Windemere to enjoy the immediate proximity to the Gulf.

Many of these properties offer desirable amenities for a comfortable stay, such as private balconies with sea views, shared swimming pools, and in-unit laundry facilities. These homes are ideal for families or groups looking for a relaxing beach getaway with all the comforts of home.
Are there any cheap holiday rentals near Windemere?
There are several affordable holiday rentals near Windemere, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around £1350 per night. Some stays even drop below that price in November 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 properties to modest family homes, providing a clean, comfortable base for adventure.

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 Windemere while keeping costs down, so you can have a comfortable stay.

*Pricing data are based on past 12 months data.
What are the top holiday rentals with pools near Windemere?
There are over 1,600 holiday rentals near Windemere offering access to swimming pools, with a wide variety of options including shared community pools, private backyard pools, and even indoor pool facilities. Properties are concentrated in areas directly around Windemere, with many properties in Perdido Key being condominiums or private homes. These rentals often feature full kitchens, Wi-Fi, and spacious living areas, making them excellent choices for families or groups seeking a comfortable stay.

When selecting your ideal rental, consider the benefits of each pool type. Private pools provide exclusivity and are great for families desiring quiet relaxation, while shared pools often include additional amenities such as fitness centres or hot tubs. For cooler months, look for heated or indoor pool options to ensure year-round enjoyment.
What are the best family holiday rentals near Windemere?
There are over 1190 family-friendly holiday homes, primarily condos and private holiday houses, in the Perdido Key area near Windemere, offering ample space and comfort for groups of all sizes. These properties often boast multiple bedrooms and bathrooms, full kitchens, and generous living areas, all designed with families in mind. With such a wide selection, you can find stays with outdoor play areas, yards, patios, and entertainment options like video games and board games, alongside essential amenities such as travel cribs, highchairs, and stair gates for younger guests.

When choosing the best fit for your family, focus on properties where adults and kids each have space to unwind, and look for homes with practical amenities like well-equipped kitchens to save on dining out. Staying nearby can mean less travel each day and more time enjoying the surroundings.
Are there any luxury holiday rentals near Windemere?
There are several luxury holiday rentals near Windemere that combine beautiful scenery with modern comfort. These properties often feature amenities such as private pools, heated pools, spa-style bathrooms with deep soaking bathtubs, private chefs, and incredible sea views or lake views.

These homes are ideal for families or larger groups, offering features like air conditioning and premium bedding for a comfortable stay. Many of these top-tier stays are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
Where should I stay when visiting Windemere?
When visiting Windemere, several excellent areas offer ideal holiday rentals. The immediate vicinity of Windemere itself provides direct access to the beautiful beaches and a relaxed coastal lifestyle. Properties here are superb for guests looking to enjoy the sun and sand with minimal travel.

Further east, towards Gulf Islands National Seashore, you'll find rentals that offer a quieter, more secluded experience, often with stunning natural views. These homes are a short drive from Windemere, making it easy to access the main attractions while enjoying a peaceful retreat.

To the west, closer to the Perdido Key State Park, rentals provide proximity to outdoor activities such as hiking and birdwatching, alongside beach access. These properties are conveniently located for exploring the natural beauty of the area.
What is the cheapest month to stay near Windemere?
The cheapest time to find holiday rentals near Windemere is typically during the late Autumn and Winter months (November to February), excluding the Christmas and New Year's weeks. November is frequently the cheapest month, often providing better deals on condos and homes, with rates often 20-25% lower than peak season. Guests can often find various savings during these months, along with greater availability of properties.
Are there any lakefront holiday rentals near Windemere
Lakefront holiday rentals near Windemere are readily available, offering a great mix of comfort, scenery, and outdoor adventure. Many are located along quiet lakes in the surrounding area. These properties are a short drive from Windemere, offering convenient access to water activities such as kayaking, fishing, or simply relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy lake views, spot local wildlife, and unwind in peaceful surroundings after exploring local trails.
Are there any top beachfront holiday rentals near Windemere
Beachfront holiday rentals near Windemere offer direct access to the sand, with many properties featuring ocean-view balconies and terraces that provide expansive views of the water. These stays are often located directly on the coastline, putting guests steps from the water. While primarily focused on beach relaxation, some locations are a short drive from lively dining and shopping areas, with quieter spots providing a peaceful environment for a relaxing stay.

Guests can enjoy amenities such as beach chairs, beach umbrellas, and often have access to oceanfront pools. Accommodation types range from comfortable ocean-facing rooms to multi-bedroom suites and private holiday houses, great for solo travellers, couples or larger groups seeking extra living space.
Are there any monthly holiday rentals near Windemere?
Vrbo offers excellent options for monthly holiday rentals near Windemere, 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 Windemere.
Are there any last-minute holiday rentals near Windemere?
Vrbo makes it simple to find last-minute holiday rentals near Windemere 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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