Winston Waterways holiday lettings

We found 75 holiday rentals — enter your dates for availability

Discover a selection of 18 homes and other holiday rentals in Winston Waterways that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, including air conditioning and Wi-Fi. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Winston Waterways

Find out more about Winston Waterways

Why visit Winston Waterways

  • Stunning Beaches: Winston Waterways boasts beautiful beaches perfect for relaxation and sunbathing.
  • Outdoor Adventures: Engage in thrilling activities such as kayaking and snorkelling in the local marine park.
  • Scenic Landscapes: Explore the lush surroundings and picturesque waterfront that define this charming area.
  • Variety of Accommodations: Choose from private holiday homes, cosy condos, and welcoming caravan parks for your stay.
  • Informative Visitor Centre: Learn about local attractions and nature through engaging exhibits and resources.

Popular types of accommodation around Winston Waterways

If you're contemplating a getaway in Winston Waterways, you're in for a treat. The most sought-after accommodations include houses, charming condos, and delightful caravan parks. Whether you're dreaming of a spacious king-size bed or the serene surroundings of Key Largo, including the inviting Don Fernando, we ensure you find the perfect place for your stay. Relax and explore with confidence, knowing we've got the ideal options for you.

  • Houses: The top choice for visitors in Winston Waterways, offering spacious and comfortable living for families, friends, or couples.
  • Condos: A popular option for those seeking a bit of luxury, these self-contained units provide modern amenities and splendid views.
  • Caravan Parks: A charming alternative for the adventurous, ideal for experiencing the outdoors while having a homey feel.
  • Villas: Elegant and often luxurious, these properties provide a serene escape with plenty of space.
  • House Boats: A unique stay on the water, perfect for those wanting a distinctive experience in a picturesque setting.**

Top attractions near Winston Waterways

Winston Waterways in Key Largo offers a delightful blend of outdoor adventures and scenic beauty, making it an ideal destination for families and solo travellers alike. Explore the local marine park, relax on the stunning beaches, or visit the informative visitor centre. With a variety of attractions catering to those seeking a beachside experience, you're sure to find plenty to enjoy during your stay.

  • John Pennekamp Coral Reef State Park: A stunning marine park just 621m from Winston Waterways, this destination offers exciting underwater adventures, including snorkelling and diving amidst vibrant coral reefs, perfect for families and thrill-seekers alike.
  • Baker's Cay Resort Beach: Located 3.1km away, this beautiful beach is ideal for relaxation, featuring soft sands and crystal-clear waters, perfect for sunbathing and enjoying the tropical atmosphere.
  • Florida Keys Visitor Center: Situated 2.5km from Winston Waterways, this centre provides a wealth of information for outdoor adventures, with family-friendly activities and insights into the local flora and fauna.

Things to do recommended for couples

For a romantic getaway in Key Largo, explore the adventurous underwater sports at Florida Keys Dive Center, just 6.8km away. Indulge in luxury at the Key Largo Anglers Club, located 9.3km from Winston Waterways, or browse the charming shops at Rain Barrel Village, also 9.3km away.

Things to do recommended for families

Families visiting Winston Waterways can splash around at Jacob's Aquatic Center, located 1.2km away, offering a fun-filled atmosphere. For a serene experience, the New Mahogany Hammock State Botanical Site, 8.7km away, provides a perfect setting for wellness and relaxation amidst nature.

Things to do recommended for groups

Enjoy a lively evening at Jimmy Johnson's Big Chill, just 1.2km from Winston Waterways, for a great atmosphere. Alternatively, visit Florida Keys Brewing Co. for a romantic brewery experience or shop at Cutler Ridge Mall, perfect for family outings and entertainment, located 11.8km away.

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

Regardless of whether you're travelling with a group, as a family, with your pets, or seeking extended stays, it's essential to filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winston Waterways with a group: Think about how many bedrooms you will require, along with features like a fully equipped kitchen or outdoor space for socialising. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Winston Waterways with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable facilities 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 Winston Waterways: For many, a family holiday wouldn’t be the same without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations supply feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winston Waterways: If you're searching for holiday rentals with 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Winston Waterways

Winston Waterways offers a delightful mix of outdoor adventure and scenic beauty, making it an ideal getaway. Located near the vibrant city of St. Petersburg, visitors can enjoy excursions that showcase the stunning waterfront and lush landscapes of West Florida. Whether you're seeking relaxation or thrilling activities, this charming neighbourhood provides a perfect backdrop for an unforgettable holiday experience.

  • Key Largo: Nestled two miles from Winston Waterways, Key Largo is an inviting island city renowned for its stunning outdoor and beach experiences. This scenic locale attracts families and adventurers alike, offering a wealth of activities. Visitors can indulge in the vibrant shopping mall centre or explore the bustling shopping area. Key Largo is home to beautiful beaches and a lively tourist precinct, making it an ideal spot for relaxation and entertainment.
  • Largo Gardens: Located a mere 186m from Winston Waterways, Largo Gardens is a charming neighbourhood that offers an invigorating outdoor and adventure experience. This area is perfect for families looking to explore its recreational facilities and shopping options. Nearby attractions include delightful beaches, a family-friendly beach, and the breathtaking national state park, ensuring that visitors have ample opportunities to connect with nature and enjoy local amenities.
  • Key Largo Village: Just 559m from Winston Waterways, Key Largo Village is a picturesque neighbourhood known for its family-friendly atmosphere and beach appeal. This area boasts an array of shopping options, including a shopping mall centre and resorts that cater to various preferences. Visitors can unwind at the local beaches and enjoy the vibrant tourist precinct, making Key Largo Village a delightful destination for those seeking a mix of relaxation and exploration.

Best time to go to Winston Waterways

If you're planning a trip to Winston Waterways, 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 September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January70.0°F (21.1°C)No Rain (Dry)Mostly SunnyModerately HighSlightly Low
February71.8°F (22.1°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March72.9°F (22.7°C)No Rain (Dry)Mostly SunnyModerately HighAverage
April76.6°F (24.8°C)No Rain (Dry)Mostly SunnyAverageAverage
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly High
July83.8°F (28.8°C)Light RainMostly SunnyAverageSlightly High
August84.4°F (29.1°C)Light RainMostly SunnyAverageAverage
September83.3°F (28.5°C)Light RainMostly SunnyModerately LowSlightly Low
October80.2°F (26.8°C)Light RainMostly SunnyModerately LowSlightly Low
November75.9°F (24.4°C)Light RainMostly SunnyModerately LowAverage
December72.9°F (22.7°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for planning your journeys. You can easily create new trips, resume from where you last stopped, or manage your existing plans. The properties you've saved or booked will be neatly organised into categories such as Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Winston Waterways?
In Winston Waterways, holiday houses are the predominant type of rental, with around 15 available throughout the area. These properties cater particularly well to families and groups, offering multiple bedrooms, spacious living areas, and fully equipped kitchens for preparing meals. Many of these houses also feature outdoor spaces such as patios or gardens, great for enjoying the warm Florida weather.
Are there any beach house rentals in Winston Waterways?
In Winston Waterways, Florida, there are approximately 21 beach house holiday rentals available. These properties are predominantly located along the scenic waterways, providing lovely views and easy access to the nearby beaches. Most beach houses come equipped with spacious living areas, fully equipped kitchens, and outdoor patios or balconies, great for enjoying the warm Florida climate. Many also feature amenities such as private pools, BBQ grills, and proximity to local attractions like parks and recreational areas, making them ideal for families or groups seeking a relaxing getaway.
How much does it cost to rent a holiday home in Winston Waterways?
Prices for holiday rentals in Winston Waterways vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winston Waterways to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winston Waterways holiday house rentals?
You can find great discounts on house rentals in Winston Waterways on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Winston Waterways holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winston Waterways with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Winston Waterways?
A long-stay holiday rental in Winston Waterways is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Winston Waterways for a holiday rental?
The most popular time to visit Winston Waterways is during October, heralding the start of the peak season that lasts until December. This month is particularly appealing for travellers seeking sunshine and outdoor adventures, as temperatures are typically warm, averaging around 27°C. It's an excellent time for enjoying water-based activities, such as kayaking or paddleboarding, while soaking up the vibrant atmosphere of the area.

As you explore Winston Waterways, you'll find an array of local parks and scenic spots great for leisurely strolls or picnics. The pleasant weather makes it comfortable to enjoy sightseeing and outdoor dining, with many establishments offering al fresco options.

For those looking for a more budget-friendly experience, April presents a wonderful opportunity. This month usually sees fewer tourists, allowing for a more peaceful getaway while still enjoying the warm climate typical of Florida. It's a fantastic time to explore nature trails or simply relax by the water's edge without the hustle and bustle of the peak season.
Are there any remote work holiday rentals in Winston Waterways?
In Winston Waterways, Florida, there are a selection of remote work holiday rentals available, with around 14 options to choose from. These properties cater to those looking to balance work and leisure, offering amenities specifically designed for remote work. Travellers can expect features such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and even computer monitors in some rentals, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Winston Waterways holiday rental?
Book your Winston Waterways holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winston Waterways home rental booking on Vrbo?
To find Winston Waterways holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winston Waterways holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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