Siesta Key Village vacation rentals

We found 1,090 vacation rentals — enter your dates for availability

Discover a selection of 174 homes, 51 apartments, and other vacation rentals in Siesta Key Village that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the amenities you need and want, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Siesta Key Village

Showing deals for:Nov 14 - Nov 21
  • Peace of mind

    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, yards and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Siesta Key Village

Find out more about Siesta Key Village

Why visit Siesta Key Village

  1. Stunning Beaches: Enjoy Siesta Key's soft, white sands and inviting atmosphere, perfect for relaxation and water activities.
  2. Charming Village Atmosphere: Explore picturesque streets filled with local art, friendly faces, and vibrant culture.
  3. Family-Friendly Activities: Engage in numerous attractions catering to families, ensuring a memorable experience for all ages.
  4. Diverse Accommodation Options: Choose from beachfront rentals, cozy condos, or spacious apartments tailored to your needs.
  5. Outdoor Adventures: Embrace outdoor pursuits with urban parks and lively streets that encourage exploration.

Popular types of accommodation around Siesta Key Village

At our customer-centric vacation rental platform, we offer an array of accommodations in Siesta Key Village, perfect for every traveller. Whether you prefer a private vacation home, a cozy condo, or a spacious apartment, we've got you covered. Our Siesta Key vacation rentals provide transparency, savings, and reassurance, ensuring a memorable stay. Explore the charm of Siesta Key Village with our diverse selection of vacation homes tailored to your needs.

  • Houses: The top choice for visitors to Siesta Key Village, offering spacious and comfortable settings perfect for families or groups.
  • Condos: A popular option for those seeking modern amenities and a convenient location, ideal for couples and solo travellers.
  • Apartments: A versatile choice for visitors, providing a homely atmosphere with essential facilities for a relaxed stay.
  • Villas: These luxurious accommodations offer a touch of elegance and privacy, perfect for a lavish getaway.
  • Cottages: A delightful option for a quaint and charming experience, great for couples or small families.**

Top attractions around Siesta Key Village

Siesta Key Village is perfect for beach, family, and urban-themed vacations. Visitors can enjoy a variety of attractions, including beautiful beaches, urban parks, and lively streets that cater to outdoor enthusiasts and families seeking city experiences. For a memorable stay, consider beachfront rentals that enhance your holiday experience in this charming village.

  1. Siesta Key Beach: Renowned for its powdery white sand and vibrant beach vibes, this stunning beach is perfect for sunbathing, swimming, and enjoying breathtaking sunsets, located 1.4km from Siesta Key Village.
  2. St. Armands Circle: A lively shopping and dining destination, this charming street features upscale boutiques and cafes, offering city vibes just 4.8km away from Siesta Key Village.
  3. Marina Jack: A picturesque marina providing access to boating and outdoor adventures, it’s an ideal spot for dining with a view, located 6.4km from Siesta Key Village.

Things to do recommended for couples

Looking for a romantic getaway in Siesta Key Village? Indulge in luxury at The Oaks Club, enjoy captivating performances at Beatrice Friedman Symphony Center, or have fun together at Evie's Golf Center. Each experience offers a unique vibe for couples seeking adventure and relaxation.

Things to do recommended for families

Families exploring Siesta Key Village can enjoy a thrilling day at Ed Smith Stadium, just 9.7km away, soak up wellness vibes at the Robert L. Taylor Community Complex 11.3km away, and venture into nature on the Canopy Walkway and Boylston Nature Trail, located 19.7km from the village.

Things to do recommended for groups

Experience the arts at Van Wezel Performing Arts Hall, explore nature on the Sarasota BayWalk hiking trail, or enjoy a round of golf at Stoneybrook Golf & Country Club. These activities offer a blend of culture, adventure, and outdoor fun for your group in Siesta Key Village.

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

When you're planning your trip, whether it's with a group, family, pets, or for an extended stay, it's important to prioritize your preferences. Here are some helpful tips for booking on Vrbo.

  • Traveling to Siesta Key Village with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for these options and much more on Vrbo.
  • Traveling to Siesta Key Village with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, as well as access to suitable amenities like private swimming pools. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Siesta Key Village: For many families, a trip wouldn’t feel whole without their furry companions. If you can relate, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Siesta Key Village: If you’re in search of vacation rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Siesta Key Village

Siesta Key Village offers a delightful blend of sun-soaked beaches and vibrant local culture, making it an ideal getaway for families and beach lovers alike. Explore the charming streets filled with art, friendly faces, and picturesque scenery. Just a stone's throw away, beautiful Siesta Key beckons with its soft, white sands and inviting atmosphere. Whether you're seeking relaxation or adventure, this Florida destination has something special for everyone.

  • Sarasota: Located a mere 8.0km from Siesta Key Village, Sarasota is a vibrant city known for its mix of beach relaxation and urban excitement. Visitors flock to Sarasota for its beautiful beaches, family-friendly activities, and cultural experiences. The downtown area features a variety of shopping centres and a lively arts scene, including galleries and theatres. Notable landmarks nearby include the stunning Lido Key Beach and the scenic family beach, making it an ideal base for both leisure and adventure.
  • Lido Key: This picturesque island, just 4.8km from Siesta Key Village, is a haven for beach lovers and families alike. Lido Key is renowned for its pristine beaches and urban parks, offering a tranquil escape with plenty of recreational opportunities. Visitors can enjoy shopping at local malls and explore vibrant dining options. The family-friendly environment makes it perfect for those looking to unwind while soaking in the sun and enjoying the company of loved ones.
  • South Sarasota: Situated 3.2km from Siesta Key Village, South Sarasota is a charming neighbourhood that combines the best of beach life with urban amenities. This area is known for its recreational spaces and family-friendly atmosphere, making it a great spot for a day of outdoor fun. Visitors can explore shopping centres and local parks, with the nearby beaches providing an idyllic setting for relaxation. South Sarasota offers a laid-back vibe, perfect for families seeking a blend of recreation and leisure.

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 January to March, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January62.6°F (17.0°C)Light RainMostly SunnyModerately HighSlightly 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 SunnyAverageSlightly 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 save on your upcoming trip? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, and easily manage your travel arrangements. You can conveniently access properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Siesta Key Village?
In Siesta Key Village, vacation houses are the most popular type of rental, with approximately 161 available throughout the area. These spacious homes often feature multiple bedrooms, fully equipped kitchens, and private outdoor spaces such as patios or gardens, making them ideal for families or groups seeking comfort and convenience. Alongside vacation houses, there are also about 77 condos and 46 apartments, providing a range of options for travellers. Condos typically include amenities like swimming pools and fitness centres, while apartments often come with kitchen facilities and living areas for a homely feel.
Are there any beach house rentals in Siesta Key Village?
In Siesta Key Village, Florida, there are approximately 642 beach house rentals available. These properties are predominantly located near the stunning Siesta Key Beach, renowned for its powdery white sands and vibrant atmosphere. Vacation rentals in this area typically feature amenities such as fully equipped kitchens, spacious living areas, and outdoor patios or balconies, great for enjoying the warm Florida evenings. Many beach houses also offer private pools, access to beach gear, and family-friendly facilities, making them ideal for those travelling with children or larger groups.
How much does it cost to rent a vacation home in Siesta Key Village?
Prices for vacation 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 travelling 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.
Are there any discounts for Siesta Key Village vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rentals in Siesta Key Village?
A long-stay vacation 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 vacation rental?
The most popular time to visit Siesta Key Village is from January to March, when the weather is at its finest and the beaches are bustling with excitement. This peak season attracts a diverse range of travellers eager to soak up the sun, enjoy water sports, and revel in the vibrant local atmosphere. During these months, you can expect pleasant temperatures averaging around 21 to 24 degrees Celsius, great for outdoor activities such as swimming, paddleboarding, or simply lounging on the powdery white sands.

January, in particular, stands out as an excellent month to visit. The crowds are just beginning to swell, making it a great time for those who enjoy a lively yet not overwhelming environment. With numerous beachside cafes and shops within walking distance, you can easily explore the local culture and indulge in fresh seafood while enjoying stunning sunset views.

For those looking for more budget-friendly options, consider planning your trip to Siesta Key Village in November. This month allows you to experience the area's charming atmosphere at a more relaxed pace. With fewer tourists around, you can enjoy the serene beaches and take advantage of lower rental rates, all while still enjoying the beautiful weather.
Are there any remote work vacation rentals in Siesta Key Village?
In Siesta Key Village, there are a significant number of remote work vacation rentals available, with approximately 274 options to choose from. This vibrant area is known for its stunning beaches and lively atmosphere, making it an ideal spot for those looking to combine work and leisure. Many properties in this locale offer amenities specifically designed for remote workers, such as high-speed Wi-Fi, dedicated desks, and comfortable office chairs. Some even feature laptop workspaces and computer monitors to ensure 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 vacation rental?
Book your Siesta Key Village vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Siesta Key Village home rental booking on Vrbo?
To find Siesta Key Village vacation 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 vacation 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.

More Vacation Rentals ideas