Siesta Key Village holiday lettings

We found 1,092 holiday rentals — enter your dates for availability

Discover a selection of 174 homes, 51 apartments and other holiday rentals in Siesta Key Village that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, which might include parking and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Siesta Key Village

Showing deals for:14 Nov - 21 Nov
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Find out more about Siesta Key Village

Find out more about Siesta Key Village

Why visit Siesta Key Village

  • Stunning Beaches: Siesta Key Beach is famous for its powdery white sand, providing the perfect spot for sunbathing and relaxation.
  • Family-Friendly Atmosphere: The village offers a charming environment suitable for family holidays, with plenty of activities for all ages.
  • Vibrant Village Life: Enjoy a leisurely stroll through the village, where friendly locals and quaint shops create a welcoming atmosphere.
  • Outdoor Activities: Explore nearby urban parks and marinas, ideal for outdoor adventures and water sports.
  • Diverse Accommodation Options: Choose from private holiday homes, cosy condos, and stylish apartments tailored to your needs.

Popular types of accommodation around Siesta Key Village

Siesta Key Village offers a delightful selection of holiday rentals, including houses, cosy condos, and stylish apartments. Whether you're seeking a family getaway or a romantic retreat, you'll find the perfect accommodation to suit your needs. With a focus on transparency and savings, our platform helps you discover the best Siesta Key holiday rentals, ensuring a memorable stay in this charming coastal destination.

  • Houses: The top choice for visitors to Siesta Key Village, offering spacious and comfortable stays for families or groups.
  • Condos: A popular selection, providing a blend of convenience and resort-like amenities for an enjoyable stay.
  • Apartments: A practical option for couples or solo travellers, these self-contained units offer flexibility and affordability.
  • Villas: A luxurious choice, featuring elegant decor and often private outdoor spaces for relaxation.
  • Cottages: Quaint and charming, these provide a cosy retreat with a homely feel for your beach getaway.**

Top attractions near Siesta Key Village

Siesta Key Village offers a delightful mix of beach, family, and city-themed holidays. Visitors can explore a variety of attractions, including stunning beaches, urban parks, and marinas, perfect for those seeking outdoor experiences. Whether you're travelling with family or enjoying a solo adventure, this charming village provides ample opportunities for memorable activities and relaxation in a picturesque setting.

  • Siesta Key Beach: Renowned for its powdery white sands and crystal-clear waters, Siesta Key Beach is the perfect spot to unwind and soak up the sun. With a relaxed atmosphere, it's ideal for swimming, sunbathing, and beach games, providing a quintessential beach experience.
  • St. Armands Circle: A vibrant shopping and dining district, St. Armands Circle offers a mix of boutique shops, restaurants, and art galleries. The lively city vibes make it a great place to explore, dine al fresco, and enjoy the local culture.
  • Marie Selby Botanical Gardens: A romantic escape, this botanical garden features stunning plant displays and serene outdoor spaces. Perfect for families, it offers educational exhibits and beautiful walking paths, making it a delightful retreat for nature lovers.

Things to do recommended for couples

For a romantic getaway in Siesta Key Village, indulge in a delightful concert at Beatrice Friedman Symphony Center, enjoy luxury at The Oaks Club, or share some fun at Evie's Golf Center. Each offers a unique experience just a short drive away, perfect for couples.

Things to do recommended for families

Your family will love the vibrant atmosphere at Ed Smith Stadium, just 3.7km from Siesta Key Village, perfect for sports enthusiasts. For a more laid-back experience, the Robert L. Taylor Community Complex, located 4.3km away, offers wellness and relaxation activities for all ages.

Things to do recommended for groups

Enjoy a night out at the Van Wezel Performing Arts Hall for a cultural experience, explore the scenic Sarasota BayWalk for a bit of adventure, or indulge in some retail therapy at Gulf Gate Mall, perfect for family and friends alike.

What do I need to keep in mind when booking a vacation around Siesta Key Village

If you're travelling with a group, family, pets, or planning an extended stay, it's essential to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Siesta Key Village with a group: Think about how many bedrooms you'll require, as well as amenities like a fully equipped kitchen or outdoor areas for group activities. Thankfully, you can easily refine your search for these features and plenty more on Vrbo.
  • Traveling to Siesta Key Village with young kids: Journeying with young children can present its own set of challenges. It's important to prioritise their comfort and safety, as well as access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Siesta Key Village: For many families, a holiday wouldn’t be the same without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Siesta Key Village: If you're in search of holiday rentals with special offers 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 accommodations. Don't forget to include additional preferences in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay near Siesta Key Village

Siesta Key Village offers a delightful blend of family-friendly charm and tropical relaxation. Stroll through the vibrant village, where friendly locals greet you, and explore the stunning Siesta Key Beach, renowned for its powdery white sand. Nearby, you’ll find other beautiful beaches and the serene Siesta Shores, perfect for unwinding. With its picturesque scenery and inviting atmosphere, your vacation here promises to be a memorable escape.

  • Siesta Key: Siesta Key is a charming island city located a mere 50m from Siesta Key Village, renowned for its stunning beaches and family-friendly atmosphere. Visitors flock to Siesta Key for outdoor experiences, indulging in sun-soaked days on the powdery sands. The area offers a variety of recreational activities, shopping options, and luxurious resorts. Notable attractions include the pristine beaches and the vibrant local community, making it a perfect spot for families and those seeking relaxation amidst nature.
  • Sarasota: Situated approximately 3.1km from Siesta Key Village, Sarasota is a vibrant city that combines beach relaxation with urban sophistication. This destination is ideal for families and those looking for a city-themed experience, featuring a plethora of shopping centres and resorts. Sarasota boasts beautiful beaches and a lively atmosphere, with local landmarks that celebrate both nature and culture. Visitors can explore parks, engage in delightful dining, and enjoy arts and cultural venues, ensuring a well-rounded holiday experience.
  • Lido Key: Located 1.9km from Siesta Key Village, Lido Key is another picturesque island that draws families and beach lovers alike. This area is celebrated for its stunning beaches and urban parks, providing a perfect blend of relaxation and recreation. Visitors can enjoy shopping at local centres and indulge in outdoor activities within the recreational areas. Lido Key’s charming beaches offer a serene escape, making it a fantastic addition to your itinerary while exploring the coastal wonders of Florida.

Best time to go to Siesta Key Village

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly Low
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.9°F (28.3°C)Light RainMostly SunnyAverageSlightly High
August83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnyModerately LowSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowSlightly Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is simple

Are you hoping to make the most of your budget on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, opting for a longer stay can lead to considerable savings. To discover a Vrbo property that suits your financial plan, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy area for you to plan new adventures, resume your previous arrangements, or view and organise your travel plans. You can easily find saved or booked properties sorted under Potential, Upcoming, or Current Trips. To begin using 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 Siesta Key Village?
In Siesta Key Village, holiday houses are the most popular type of rental, with approximately 161 available throughout the area. These homes typically provide spacious living conditions, including multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or decks, superb for enjoying the warm Florida weather. Many are situated close to the beautiful Siesta Key Beach and the lively village centre, making them ideal for families or larger groups looking to enjoy both relaxation and local attractions.
Are there any beach house rentals in Siesta Key Village?
In Siesta Key Village, Florida, there are approximately 642 beach house rentals available, making it a popular destination for holidaymakers. These beach houses often come equipped with amenities that enhance the coastal experience, such as private pools, direct beach access, fully equipped kitchens, and spacious outdoor patios great for entertaining or relaxing in the sun. Many rentals also feature multiple bedrooms and bathrooms, accommodating families or larger groups comfortably. The village's proximity to the stunning Siesta Beach and various dining and shopping options adds to the appeal, providing visitors with both convenience and leisure.
How much does it cost to rent a holiday home in Siesta Key Village?
Prices for holiday rentals in Siesta Key Village 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 Siesta Key Village 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 Siesta Key Village holiday house rentals?
You can find great discounts on house rentals in Siesta Key Village 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 Siesta Key Village holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Siesta Key Village 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 Siesta Key Village?
A long-stay holiday rental in Siesta Key Village 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 Siesta Key Village for a holiday rental?
January marks the beginning of the peak season in Siesta Key Village, attracting sun-seekers and beach lovers eager to bask in the warm Florida sunshine. This vibrant month kicks off the high tourist season that lasts until March, when visitors flock to the area to enjoy its pristine beaches and crystal-clear waters. With temperatures typically ranging from the mid to high 20s Celsius, January offers superb conditions for outdoor activities such as swimming, sunbathing, and leisurely strolls along the shore.

During this peak season, you'll find an array of local events and festivals that showcase the lively charm of Siesta Key. From art shows to beach parties, the atmosphere is buzzing with excitement, providing ample opportunities for socialising and enjoying the local culture.

If you're looking for a more budget-friendly option, consider visiting in November. This month sees fewer tourists, allowing you to enjoy the same stunning beaches and delightful weather without the crowds. The ocean remains warm, making it a lovely time for beach walks and other outdoor pursuits, all while taking in the beautiful sunsets unique to this coastal paradise.
Are there any remote work holiday rentals in Siesta Key Village?
In Siesta Key Village, there are numerous remote work holiday rentals available, with a total of around 274 options to choose from. This vibrant coastal area is renowned for its stunning white-sand beaches and lively atmosphere, making it a great choice for those looking to blend work and leisure. Many of the properties are equipped with dedicated workspaces, including desks and comfortable chairs, 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 Siesta Key Village holiday rental?
Book your Siesta Key Village 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.
What are the top attractions in Siesta Key Village?
In Siesta Key Village, visitors can enjoy a vibrant array of attractions that showcase the area's charm. The village is renowned for its beautiful beaches, particularly Siesta Beach, famous for its powdery white sand and stunning sunsets. Holiday rentals in this area often provide convenient access to the beach, allowing for easy enjoyment of sunbathing, swimming, and water sports.

The village itself is lively, with a variety of shops, restaurants, and cafes lining the streets. Visitors can explore local boutiques for unique souvenirs or indulge in fresh seafood at nearby waterfront dining spots. The atmosphere is particularly festive during the evening, with live music and entertainment often available in the village squares.
Can I change or cancel my Siesta Key Village home rental booking on Vrbo?
To find Siesta Key Village 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 Siesta Key Village 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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