Waterside holiday lettings

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Why visit Waterside

  • Idyllic coastal walks: Stroll along the stunning shores of Fort Myers Beach for breathtaking views.
  • Family-friendly activities: Enjoy a variety of outdoor experiences suitable for visitors of all ages.
  • Charming accommodation: Choose from delightful waterside cottages and modern villas tailored to your needs.
  • Exciting boat tours: Explore the waters with thrilling boat excursions that showcase the area's natural beauty.
  • Friendly local atmosphere: Experience the warm hospitality of the locals, enhancing your holiday experience.

Popular types of accommodation around Waterside

At Vrbo, we offer a delightful selection of waterside vacation rentals in Waterside, including charming waterside cottages, modern condos, and luxurious villas. Whether you're seeking a cosy retreat for a romantic getaway or spacious holiday accommodation for the whole family, our options cater to every need. Explore the beauty of Waterside with the perfect holiday home that promises transparency, savings, and reassurance for your next waterside holiday.

  • Houses: This is the top choice for visitors to Waterside, offering spacious accommodations ideal for families, friends, or couples seeking privacy and comfort.
  • Condos: A popular option for those wanting modern amenities and communal facilities, perfect for a sociable stay.
  • Villas: These luxurious retreats provide ample space and often include private pools, ideal for a lavish getaway.
  • Apartments: A great choice for a more independent experience, combining convenience with homely comforts.
  • Cottages: Quaint and charming, these cosy abodes are perfect for a peaceful escape near the beach.**

Top attractions near Waterside

Waterside in Fort Myers Beach offers a delightful blend of attractions, perfect for beach lovers and families seeking outdoor experiences. Visitors can enjoy idyllic coastal walks, relaxing cottage holidays, and exciting boat tours. With a stunning beach, nearby urban parks, and modern educational institutions, Waterside is an exceptional destination for memorable holidays by the water.

  • Bonita Springs Public Beach: Located a mere 2.5km from Waterside, this stunning beach offers a relaxing atmosphere with soft sands and warm waters, perfect for sunbathing and leisurely walks along the shoreline.
  • Florida Gulf Coast University: Just 5.0km away, this modern university boasts a vibrant campus with a youthful energy, featuring various cultural events and activities that reflect city life.
  • Hertz Arena: Situated 4.3km from Waterside, this entertainment venue is ideal for family outings, showcasing concerts, sports events, and shows that cater to all ages.

Things to do recommended for couples

For a romantic getaway near Waterside, try a round of mini-golf at Jungle Golf Ft. Myers for some playful competition, or explore the underwater wonders at Sanibel Sea School. For ultimate relaxation, unwind together at Brookshire Bath and Tennis Club's serene spa.

Things to do recommended for families

Your family will have a delightful time at Mound Key Archaeological State Park, perfect for relaxation, only 1.2km from Waterside. For a bit of adventure, head to Beach Bowl, an exciting arcade situated 3.7km away. Don't miss the sports action at Lee Health Sports Complex, 5.6km distant.

Things to do recommended for groups

Groups visiting Waterside can enjoy shopping at Coconut Point Mall, located 3.1km away, or tee off at Raptor Bay Golf Club, merely 1.9km away. For a nautical adventure, explore Naples Marina and Excursions, situated 6.2km from Waterside.

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

If you’re planning a trip with friends, family, or even bringing your pets along, or if you're considering a longer stay, it's important to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Waterside with a group: Think about how many bedrooms you require, as well as amenities like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these features and much more on Vrbo.
  • Traveling to Waterside with young kids: Travelling with young children can present its own set of challenges. It’s important 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 Waterside: For many, a family holiday isn’t truly fulfilled without their furry companion joining in. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Waterside: If you’re seeking holiday rentals with discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. You might also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Waterside

Waterside, Fort Myers Beach, is a delightful destination where friendly locals and family-friendly activities abound. Enjoy stunning waterside views while exploring relaxing lodges and budget-friendly excursions. Whether you're seeking a peaceful holiday by the water or planning your next seaside break, this charming locale offers a perfect blend of tranquillity and adventure, making it an ideal spot for your next holiday getaway.

  • Fort Myers Beach: Located a mere 3.1km from Waterside, Fort Myers Beach is a vibrant coastal city that attracts visitors seeking sun-soaked shores and a lively atmosphere. This destination is perfect for families and outdoor enthusiasts, with a variety of resorts and recreation centres to choose from. The stunning beach, known for its soft sands and gentle waves, is ideal for sunbathing and water sports. Nearby, you'll find a shopping mall centre offering an array of dining and retail options, making it a convenient stop for all your holiday needs.
  • Sanibel: Situated 5.6km from Waterside, Sanibel is a charming island city renowned for its beautiful beaches and abundant wildlife. Ideal for families and outdoor lovers, visitors can partake in a range of activities from beachcombing to exploring local parks and recreational areas. The beaches here are famous for their shell-collecting opportunities, while the laid-back atmosphere makes it a perfect spot for relaxation. Sanibel also features delightful shopping spots and dining options, enhancing your travel experience.
  • Bonita Springs: Just 5.0km from Waterside, Bonita Springs is a picturesque city that offers a fantastic blend of beach life and outdoor adventure. Known for its family-friendly environment, it boasts several recreation centres and resorts, as well as golf courses for those looking to tee off. The local beaches provide a tranquil escape, while the nearby island attractions ensure there’s plenty to explore. Bonita Springs is a remarkable destination for anyone seeking both relaxation and adventure during their holiday.

Best time to go to Waterside

If you're planning a trip to Waterside, 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January64.8°F (18.2°C)No Rain (Dry)Mostly SunnyHighAverage
February67.3°F (19.6°C)No Rain (Dry)SunnyHighAverage
March69.8°F (21.0°C)No Rain (Dry)SunnyHighSlightly High
April74.8°F (23.8°C)Light RainMostly SunnyAverageSlightly High
May78.6°F (25.9°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Moderate RainMostly SunnyAverageAverage
July83.5°F (28.6°C)Moderate RainMostly SunnyAverageAverage
August83.7°F (28.700000000000003°C)Moderate RainMostly SunnyLowSlightly Low
September82.2°F (27.9°C)Moderate RainMostly SunnyLowSlightly Low
October78.4°F (25.8°C)Light RainMostly SunnyLowSlightly Low
November72.5°F (22.5°C)No Rain (Dry)Mostly SunnyAverageAverage
December68.5°F (20.3°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you might find considerable savings by opting for a longer stay. To locate a Vrbo property that suits your budget, feel free to use our filters to narrow down your search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a dedicated area for you to design new journeys, manage your existing plans, and review your reservations. The properties you've saved or booked are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about 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 Waterside?
The best holiday rentals near Waterside are typically located in the South Island neighbourhood of Fort Myers Beach, Florida. You will find a wide array of options, from stylish condos with ocean views to private holiday houses superb for a family getaway. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You can easily find the best holiday rentals near Waterside within a short distance of the attraction.

Many of these holiday rentals offer desirable amenities such as a private balcony for enjoying the sea breeze, access to a shared pool for a refreshing dip, and laundry facilities for your convenience. These properties are ideal for couples or small families looking for a relaxing beach holiday.
Are there any cheap holiday rentals near Waterside?
There are several affordable holiday rentals near Waterside, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around £110 per night in areas like South Island. Some stays even drop below this price in September and October 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 condos 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 Waterside 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 Waterside?
There are hundreds of pet-friendly holiday rentals near Waterside, with 379 properties available. These rentals are predominantly condos and private holiday houses located in the South Island area of Fort Myers Beach. Many offer amenities specifically for pets, such as private decks and easy outdoor access, alongside essential comforts for guests like full kitchens and Wi-Fi.

When searching for the best pet-friendly holiday rentals near Waterside, remember to check individual house rules regarding pet size restrictions and any additional fees.
What are the top holiday rentals with pools near Waterside?
Near Waterside, there are over 1,185 holiday rentals offering access to swimming pools. Guests can choose from a wide variety, including properties with private backyard pools, shared community pools, and even some with indoor options. These properties are concentrated in the South Island area of Fort Myers Beach, with many being condos or private holiday houses. Standard amenities often include full kitchens, multiple bedrooms, Wi-Fi, and outdoor spaces, making them well-suited for families or groups seeking a comfortable stay.

When selecting your ideal home, consider the type of pool that best suits your preferences. Private pools provide seclusion and are excellent for families, while shared pools often come with additional facilities like fitness centres or hot tubs. For cooler months, many properties offer heated or indoor pools, ensuring year-round enjoyment. It is always a good idea to check availability, especially for peak season dates, to secure your preferred option.
What are the best family holiday rentals near Waterside?
There are over 1,000 family-friendly holiday homes in the South Island region near Waterside, 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, gardens, and patios where kids can play, as well as WiFi for downtime, and washer/dryers to handle laundry during the trip.

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 means less travel time each day and more time enjoying the area.
Are there any luxury holiday rentals near Waterside?
Near Waterside, guests can find several luxury holiday rentals that combine scenic views with modern comfort. These properties often feature amenities such as private pools, rainfall showerheads, deep soaking bathtubs, and private beach access. Many also offer resort views or lake views, and some include access to onsite golf or tennis facilities.

These homes are ideal for families or larger groups, providing conveniences like air conditioning and private chefs in some cases. 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 Waterside?
Holiday rentals near Waterside offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around £110 per night, providing an affordable option near the Waterside. Mid-range rentals, including private homes, are generally around £205 per night, offering more comfort and privacy. For those seeking a more luxurious experience, upscale options can cost £260 or more per night, often featuring additional space or premium amenities.

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 Waterside?
When visiting Waterside, South Island is a prime location, offering numerous holiday rentals with stunning waterfront views and direct access to the beach. Properties here provide a relaxed coastal vibe, superb for those seeking sun and sand.

For those looking for a slightly different experience, the northern part of Fort Myers Beach, while a short drive from Waterside, provides a range of properties that are still very convenient for accessing the attraction. This area offers a mix of quiet residential streets and proximity to local shops and eateries.
What is the cheapest month to stay near Waterside?
The cheapest time to find holiday rentals near Waterside is typically during the late Summer to early Autumn (September to October). September is frequently the single cheapest month, often providing lower rates on properties and better deals compared to the peak season. Guests can often find various savings during these months, along with greater availability of holiday rentals.
Are there any lakefront holiday rentals near Waterside
Lakefront holiday rentals are available near Waterside, primarily situated on nearby lakes and canals that offer direct water access. These properties are a short drive from Waterside, offering convenient access to water activities such as kayaking, fishing, swimming, or 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 the water views and outdoor activities.
Are there any top beachfront holiday rentals near Waterside
Beachfront holiday rentals near Waterside are predominantly found on South Island, offering direct access to the sand. Many properties boast ocean-view balconies or are just steps from the water, providing guests with prime views of the Gulf of Mexico. Guests can find properties within walking distance of lively dining, nightlife, and shopping areas, while slightly quieter spots offer a more relaxed environment for those seeking tranquillity.

Guests staying near Waterside can enjoy amenities such as beach chairs, umbrellas, and oceanfront pools. A variety of accommodation types are available, from ocean-facing rooms and suites to multi-bedroom units with private terraces, suiting different group sizes and preferences.
Are there any monthly holiday rentals near Waterside?
Vrbo offers excellent options for monthly holiday rentals near Waterside, 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 Waterside.
Are there any last-minute holiday rentals near Waterside?
Vrbo makes it simple to find last-minute holiday rentals near Waterside 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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