We found 160 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals within easy reach of Windsor Beach that provide the perfect home base for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you expect for your stay, such as parking and air conditioning. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value
Frequently asked questions
What are the best holiday rentals near Windsor Beach?
The best holiday rentals near Windsor Beach are typically located in Tucker's Town, offering stunning views and convenient access to the shoreline. You will find a great selection of properties, with many guests choosing between comfortable apartments superb for couples or smaller groups, and private holiday houses providing more space and privacy. If you are willing to drive a bit further, renting in nearby areas can be an affordable option. Searching for the best holiday rentals near Windsor Beach often yields results with direct beach access or close proximity to the water.
Many of these holiday rentals come with desirable amenities so you can have a comfortable stay, such as a deck or patio for enjoying the sea breeze, and air conditioning which is essential for warmer days. These homes are ideal for families or groups seeking a relaxing beach holiday.
Are there any cheap holiday rentals near Windsor Beach?
There are several affordable holiday rentals near Windsor Beach, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$200 per night. Some stays even drop below AU$150 per night in November during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include amenities such as WiFi, toiletries, and self-parking, and can range from cosy apartments to modest private homes, providing a clean, comfortable base for adventure.
To get the best value, consider staying slightly outside the immediate vicinity of Windsor Beach. 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 Windsor Beach while keeping costs down.
*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Windsor Beach?
Several pet-friendly holiday rentals are available near Windsor Beach, primarily consisting of villas and private holiday houses. These properties, located in and around Tucker's Town, offer comfortable stays for guests and their canine companions. Many feature amenities such as private outdoor areas and easy access to natural surroundings, ensuring both guests and pets can enjoy their time.
For those seeking the best pet-friendly holiday rentals near Windsor Beach, it is always advisable to review the specific house rules regarding pet size or any additional fees. Windsor Beach itself welcomes leashed dogs, offering ample space for them to roam.
What are the top holiday rentals with pools near Windsor Beach?
There are approximately 16 holiday rentals near Windsor Beach featuring swimming pools, offering a mix of private outdoor pools and shared community facilities. These properties are primarily found in Tucker's Town and surrounding areas, providing guests with options ranging from private holiday houses to apartments. Most rentals come equipped with standard amenities such as full kitchens, Wi-Fi, and outdoor spaces, making them suitable for families or groups seeking a comfortable and convenient stay.
When selecting your ideal rental, consider the benefits of each pool type. Private pools provide seclusion and are superb for families desiring an exclusive swimming experience, while shared pools often offer access to additional facilities. Many outdoor pools in Bermuda are ideal for enjoyment during the warmer months, but for cooler periods, it is advisable to check for heated options.
What are the best family holiday rentals near Windsor Beach?
There are approximately 20 family-friendly holiday homes near Windsor Beach, primarily private holiday houses and apartments, offering ample space and comfort for groups of all sizes. These properties often boast multiple bedrooms and bathrooms, full kitchens for meal preparation, and generous living areas, all designed with families in mind. Many stays also feature outdoor play areas, gardens, yards, or patios, along with washer/dryers for convenience, and entertainment options such as books and video games.
When choosing the best fit for your family, focus on properties that offer separate spaces for adults and children, and look for homes with practical amenities like well-equipped kitchens and laundry facilities to make your stay smoother. Staying nearby means less travel time and more opportunities to enjoy Windsor Beach.
Are there any luxury holiday rentals near Windsor Beach?
There are several luxury holiday rentals near Windsor Beach that combine beautiful scenery with modern comfort. Guests can find properties featuring amenities such as private pools, private beach access, and gourmet kitchens, as well as an onsite private chef service. Many homes offer stunning lake views and are equipped with air conditioning and fireplaces.
These homes are ideal for families or larger groups, providing plenty of space and comfort. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a pleasant and professional experience.
Where should I stay when visiting Windsor Beach?
When planning your stay near Windsor Beach, several fantastic areas offer unique advantages for your holiday rental. For those seeking direct access to beautiful pink sand and crystal-clear waters, properties within Tucker's Town itself provide unparalleled convenience. This exclusive parish offers a selection of luxurious homes and estates, superb for guests desiring privacy and high-end amenities.
Another excellent option is the area around Harrington Sound. While a short drive from Windsor Beach, this region offers stunning waterfront properties with private docks, ideal for those interested in boating, kayaking, or simply enjoying serene water views. Properties here provide a peaceful retreat with easy access to various activities across the island.
For a more active and vibrant experience, consider holiday rentals in the nearby town of St. George's. This historic town, a UNESCO World Heritage site, is a short drive from Windsor Beach and offers a charming collection of traditional Bermudian homes. Guests staying in St. George's can explore historical forts, quaint shops, and local eateries, all while being conveniently located for trips to the beach.
What is the cheapest month to stay near Windsor Beach?
The cheapest time to find holiday rentals near Windsor Beach is typically during the late Autumn to early Winter (November to February), excluding the Christmas and New Year's weeks. November is frequently the cheapest month, often providing the best deals on properties and homes. Guests can often find lower rates during these months, along with greater availability, with prices often 20-30% less than peak season.
Are there any lakefront holiday rentals near Windsor Beach
Yes, lakefront holiday rentals are available near Windsor Beach, primarily situated along the various coves and inlets that characterise Bermuda's picturesque coastline. These properties are a short drive from Windsor Beach, offering convenient access to water activities such as kayaking, fishing, swimming, or simply relaxing by the shore. Guests can also enjoy paddleboating, motorboating, parasailing, and sailing from nearby locations.
These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy stunning water views and partake in various water sports.
Are there any top beachfront holiday rentals near Windsor Beach
Beachfront holiday rentals near Windsor Beach offer direct access to the sand, with many properties boasting ocean-view balconies or terraces just steps from the water. These stays are often situated along the coast of Tucker's Town, providing a peaceful setting for relaxation. While Windsor Beach itself is more secluded, these rentals are a short drive from lively dining and shopping options in nearby areas.
Guests can often find properties equipped with beach chairs, umbrellas, and beach towels for a comfortable day by the sea. Many units feature ocean-facing rooms, suites, or multi-bedroom layouts, ideal for groups or families seeking extra living space.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.
Stayz 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 Stayz?
Stayz'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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.
Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.