Siesta Key Village vacation rentals

We found 1,190 vacation rentals — enter your dates for availability

Discover a selection of 174 homes, 48 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 7 - Nov 14

Image gallery for Charming Chic Getaway - 2 min. Walk to Beach, Restaurants, & Shops

Living area
10 out of 10 rating
Exceptional
(10 reviews)

Charming Chic Getaway - 2 min. Walk to Beach, Restaurants, & Shops

Siesta Key, FL

21% off
Price is $306
$2,141 for 7 nights
All fees included
Charming Chic Getaway - 2 min. Walk to Beach, Restaurants, & Shops

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Find out more about Siesta Key Village

Find out more about Siesta Key Village

Why visit Siesta Key Village

  1. Beautiful Beaches: Enjoy the stunning Siesta Key Beach, known for its soft, white sand and crystal-clear waters, perfect for sunbathing and swimming.
  2. Family-Friendly Activities: Engage in various outdoor adventures, from beach games to exploring nearby parks, ideal for all ages.
  3. Charming Village Atmosphere: Stroll through Siesta Key Village's quaint shops, art galleries, and vibrant local culture.
  4. Delicious Dining: Savor a diverse range of dining options, from casual beachside eateries to upscale restaurants.
  5. Stunning Sunsets: Witness breathtaking sunsets that paint the sky with vibrant colors, creating unforgettable memories.

Popular types of accommodation around Siesta Key Village

Planning a getaway to Siesta Key Village? You've made a fantastic choice! Discover the charm of this coastal paradise by exploring a variety of vacation rentals, including beautiful condos, houses, and convenient apartments. Whether you're seeking beach access, friendly private pool rentals, or a cozy spot in the heart of Siesta Key Village, you're sure to find the perfect accommodation for your unforgettable vacation.

  • Condos: The top choice for vacation rentals in Siesta Key Village, offering modern amenities and community features.
  • Houses: Ideal for families or groups, these homes provide a spacious and comfortable home-away-from-home experience.
  • Apartments: A convenient option for couples or solo travelers, with various sizes and styles available.
  • Cottages: Quaint and charming, these rentals provide a cozy atmosphere perfect for a relaxing getaway.
  • Villas: Luxurious and spacious, villas are perfect for those seeking an upscale vacation experience.**

Top attractions around Siesta Key Village

Siesta Key Village offers a perfect blend of beach, family, and outdoor activities. Visitors can explore beautiful beaches, urban parks, and nearby national and state parks, ideal for a memorable vacation. Whether you're interested in island hopping or simply soaking up the sun on Siesta Key Beach, there's something for everyone. Enjoy a relaxing getaway with ample opportunities for outdoor adventures and family experiences in this charming coastal destination.

  1. Siesta Key Beach: Renowned for its powdery white sand and turquoise waters, Siesta Key Beach offers a perfect setting for sunbathing, swimming, and beach activities. Its relaxed atmosphere makes it a favorite for families and couples alike, providing stunning sunsets and a vibrant beach vibe.
  2. St. Armands Circle: A charming, upscale shopping and dining district, St. Armands Circle features boutique stores, art galleries, and gourmet restaurants. With its lively city vibe, it’s an ideal spot for leisurely strolls and enjoying outdoor cafes.
  3. IMG Academy: A premier sports training facility, IMG Academy offers world-class coaching and programs for athletes of all levels. Visitors can explore the campus, attend events, or even participate in training sessions, making it a unique experience for sports enthusiasts.

Things to do recommended for couples

For a romantic getaway in Siesta Key Village, indulge in luxury at The Oaks Club, enjoy enchanting performances at the Beatrice Friedman Symphony Center, or have some fun together at Fish Hole Miniature Golf. Each spot offers a unique experience perfect for couples looking to create lasting memories.

Things to do recommended for families

Your family vacation in Siesta Key Village can include exciting visits to Ed Smith Stadium for sports thrills, Nathan Benderson Park for wellness and relaxation, and the Robert L. Taylor Community Complex, where you can enjoy various recreational activities together. Fun awaits just a short drive away!

Things to do recommended for groups

Experience the vibrant Mall at University Town Center for shopping, enjoy a show at the romantic Van Wezel Performing Arts Hall, or embark on an adventurous hike at Sarasota BayWalk, all within a short drive from Siesta Key Village. Perfect for group fun and exploration!

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

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

  • Traveling to Siesta Key Village with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Siesta Key Village with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Siesta Key Village: For many families, a vacation wouldn't feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Siesta Key Village: If you're seeking vacation 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 rentals. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay around Siesta Key Village

Siesta Key Village is a perfect island getaway, boasting beautiful beaches and a family-friendly atmosphere. Visitors can enjoy relaxing days under the sun, explore charming shops and art galleries, and indulge in delicious dining options. With a welcoming community and an abundance of outdoor activities, Siesta Key is ideal for families looking to make unforgettable vacation memories in Florida. Don’t miss the stunning sunsets and the vibrant local culture that make this destination truly special.

  • Sarasota: Located approximately 5 miles from Siesta Key Village, Sarasota is a vibrant city known for its beautiful beaches and family-friendly atmosphere. Visitors can enjoy a wealth of outdoor activities, from sunbathing on the stunning shoreline to exploring the local parks. The city features a variety of shopping options, including a bustling mall and charming boutiques. Sarasota is also famous for its cultural attractions, such as the Ringling Museum of Art, which showcases impressive art collections and stunning gardens.
  • Bradenton: Situated about 15 miles from Siesta Key Village, Bradenton offers a delightful mix of beach fun and outdoor adventures. This city is perfect for families, with numerous recreational opportunities and educational venues. Golf enthusiasts will appreciate the well-maintained courses, while sports fans can catch a game at local stadiums. The area's beaches provide a relaxing atmosphere for sunbathing and water activities, making it an ideal destination for a day trip.
  • Longboat Key: Just 11 miles from Siesta Key Village, Longboat Key is a picturesque barrier island known for its upscale residential areas and pristine beaches. This destination attracts families and outdoor lovers alike, offering a range of activities from shopping at local centers to enjoying recreational facilities. Visitors can unwind on the family-friendly beaches or explore the charming town neighborhoods, which feature delightful dining options and boutique shops, ensuring a memorable experience on your vacation.

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 in February to March and July, 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 SunnySlightly LowAverage
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverageSlightly High
March68.0°F (20.0°C)No Rain (Dry)SunnySlightly HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnySlightly 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 SunnySlightly HighAverage
August83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnySlightly LowSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyAverageSlightly Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? Keeping your travel dates flexible can be a great way to take advantage of fluctuating prices. Additionally, choosing to book a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you make informed choices and get the most out of your travel experience.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a convenient way to plan your trips, pick up where you left off, and manage your travel arrangements. You can easily find your saved and booked properties organized into Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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 accommodation, with about 165 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, and private outdoor spaces for enjoying the warm Florida weather. Many houses are situated close to the beach, providing easy access to the stunning shores of Siesta Key.

Additionally, there are approximately 75 condos and 41 apartments that offer a range of amenities such as fully equipped kitchens, pools, and communal areas for socializing. For those seeking a more quaint experience, several chalets and cottages are also available, often located in lush surroundings and providing a cozy atmosphere.
Are there any beach house rentals in Siesta Key Village?
In Siesta Key Village, Florida, there are approximately 685 beach house rentals available. These properties range from charming cottages to larger homes, suiting various group sizes and preferences. Most beach houses come equipped with modern amenities, including fully stocked kitchens, spacious living areas, and private outdoor spaces like patios or decks great for enjoying the warm Florida sun. Many rentals are conveniently located near the famous Siesta Key Beach, providing easy access to its powdery white sands and vibrant local attractions. Find your rental near the beach in Siesta Key Village.
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 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 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.
What are popular rental amenities in Siesta Key Village?
In Siesta Key Village, travelers can expect a range of popular rental amenities that enhance their vacation experience. Most rentals feature fully equipped kitchens, allowing guests to prepare their own meals and enjoy dining in. Many properties also include heated pools, superb for relaxing and swimming regardless of the weather. For those who appreciate a good cup of coffee, rentals are often equipped with coffee and tea makers. Outdoor spaces like patios are common, providing a pleasant area for guests to unwind and soak up the sun.
Are there any family house rentals in Siesta Key Village?
In Siesta Key Village, Florida, there are plenty of family-friendly house rentals available—around 210 in total. This vibrant area offers a mix of spacious homes that cater to families looking for a comfortable getaway. Many of these properties come equipped with full kitchens, allowing for convenient home-cooked meals, and ample living space where everyone can gather and relax together.

The locale is just a short stroll from the beautiful Siesta Key Beach, renowned for its soft, white sand and clear waters, making it ideal for families looking to spend time by the sea. See all family-friendly rentals in Siesta Key Village.
Can I rent a vacation home with a pool or hot tub in Siesta Key Village?
In Siesta Key Village, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with around 191 options for properties with pools and 49 with hot tubs. This charming beach community is known for its beautiful white-sand beaches and vibrant atmosphere. Many of the rentals in this area come with desirable amenities such as private pools, relaxing hot tubs, outdoor patios, and fully equipped kitchens, ideal for enjoying a relaxing getaway by the sea.

Travelers can expect to find properties close to the beach, allowing easy access for sunbathing, swimming, and water sports. Some homes may also include features like barbecue grills, lush landscaping, and spacious living areas, making them great for family gatherings or socializing with friends. Find your rental in Siesta Key Village with a pool or a hot tub.
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 travelers 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.
Are there pet-friendly vacation rentals in Siesta Key Village?
Yes, you can book pet-friendly vacation rentals in Siesta Key Village, where there are numerous options available for travelers looking to bring their furry friends along. The village is known for its beautiful beaches and a vibrant atmosphere, making it a great destination for both relaxation and fun. Vacation rentals in this area often feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like patios or balconies, great for enjoying the warm Florida weather.

Siesta Key Village is conveniently located near several pet-friendly parks and beach areas, allowing for enjoyable outings with your pets. The nearby Siesta Beach is known for its soft, white sand and has designated pet-friendly times, making it ideal for morning or evening strolls with your dog. Additionally, the village is home to various pet-friendly cafes and shops, ensuring that you and your pet feel welcome throughout your stay. See all pet-friendly rentals in Siesta Key Village.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Siesta Key Village for a vacation rental?
January is the most popular time to visit Siesta Key Village, attracting sun-seekers eager to enjoy its beautiful beaches and vibrant atmosphere. The peak season runs from January to March, when visitors flock to this picturesque destination to bask in warm temperatures, typically ranging from the mid-60s to low 80s Fahrenheit. This time of year is great for outdoor activities, as you can indulge in swimming, sunbathing, and beachside strolls along the powdery white sands that Siesta Key is famous for.

During these bustling months, the village comes alive with events and activities, making it an ideal spot for travelers who enjoy a lively atmosphere. You can explore local shops, dine at charming restaurants, and participate in various water sports that cater to adventure enthusiasts.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to soak in the serene beauty of Siesta Key without the crowds. You can still enjoy pleasant weather and the area's natural attractions, which are just as inviting during the shoulder season.

Ultimately, the best time to book a vacation rental in Siesta Key Village depends on whether you prefer the vibrant energy of peak season or the tranquil charm of the off-peak period.
Are there any remote work vacation rentals in Siesta Key Village?
In Siesta Key Village, there are numerous vacation rentals suitable for remote work, with around 259 options available. This vibrant area, known for its stunning beaches and lively atmosphere, provides a superb backdrop for balancing work and leisure. Many of these rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, ergonomic desk chairs, and laptop workstations, ensuring that you can stay productive during your stay.

The proximity to the beautiful Siesta Key Beach allows for quick breaks to enjoy the sun and sand, while the charming village itself offers plenty of dining and shopping options to explore after work hours. 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.
What are the top attractions in Siesta Key Village?
In Siesta Key Village, visitors can enjoy a variety of attractions that highlight the area's charm and natural beauty. The village itself is known for its vibrant atmosphere, featuring shops, restaurants, and art galleries that offer a taste of local culture. The famous Siesta Beach, frequently rated as one of the best beaches in the United States, is just a short walk away, boasting powdery white sand and crystal-clear waters great for sunbathing and swimming.

The nearby Siesta Key Public Beach offers amenities such as picnic areas, volleyball courts, and a playground, making it an ideal spot for families. For those interested in outdoor activities, the area provides opportunities for kayaking and paddleboarding, with rentals available from local businesses. Additionally, the nearby Turtle Beach offers a more tranquil setting, where visitors can relax and enjoy stunning sunsets.

Exploring the local dining scene in Siesta Key Village is also a highlight, with a variety of options ranging from casual beachside eateries to more upscale restaurants, many featuring fresh seafood and local ingredients.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy 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.

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