Siesta Key Village vacation rentals

We found 1,091 vacation rentals — enter your dates for availability

Discover a selection of 174 homes, 53 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:Dec 12 - Dec 19

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10 out of 10 rating
Exceptional
(41 reviews)

Siesta Key Retreat Sarasota Florida

Siesta Key, FL

9% off
Price is $1,568
$10,978 for 7 nights
All fees included
Siesta Key Retreat Sarasota Florida

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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 features powdery white sand and a vibrant atmosphere, perfect for relaxation.
  • Family-Friendly Activities: The area offers a variety of outdoor activities suitable for families, ensuring fun for all ages.
  • Charming Village Atmosphere: Siesta Key Village boasts a welcoming vibe with friendly locals and a tropical setting.
  • Diverse Accommodations: Choose from a range of vacation rentals, including cozy condos and spacious homes for a comfortable stay.
  • Urban Parks and Marina: Explore nearby urban parks and a marina, enhancing your outdoor experience in this picturesque location.

Popular types of accommodation around Siesta Key Village

Planning a getaway to Siesta Key Village? You're in for a treat. Discover a range of popular vacation rentals, including houses, condos, and apartments. Whether you're seeking a cozy Siesta Key condo or a spacious vacation home, our selection of Siesta Key Island rentals has something for everyone. Enjoy the flexibility and comfort of vacation rental properties that make your stay truly unforgettable.

  • Houses: The top choice for visitors in Siesta Key Village, offering spacious accommodations for families and groups seeking comfort and privacy.
  • Condos: A popular option that provides the convenience of amenities and often stunning views, perfect for couples and small families.
  • Apartments: Ideal for travelers looking for a home-away-from-home experience with essential facilities and a cozy atmosphere.
  • Villas: Elegant and luxurious, these rentals offer upscale living with ample space and often private pools.
  • Cottages: Quaint and charming, perfect for a quaint getaway with a touch of nostalgia.**

Top attractions near Siesta Key Village

Siesta Key Village is perfect for beach lovers and families seeking a city-themed vacation. With beautiful beaches, urban parks, and a marina, visitors can enjoy a variety of outdoor activities and family-friendly experiences. Whether you're looking to relax by the shore or explore local attractions, Siesta Key Village has something for everyone, making it an ideal destination for a memorable getaway.

  • Siesta Key Beach: Famous for its powdery white sand and stunning sunsets, Siesta Key Beach offers a relaxing atmosphere with plenty of space for sunbathing, swimming, and beach activities. Located 0.9 miles from Siesta Key Village, it's an ideal spot for soaking up the sun and enjoying the tropical vibes.
  • St. Armands Circle: Situated 3 miles from Siesta Key Village, St. Armands Circle boasts a vibrant shopping and dining scene. This charming area has a distinct city vibe, lined with boutiques, cafes, and art galleries, perfect for leisurely strolls and people-watching.
  • Marina Jack: Located 4 miles away, Marina Jack is a picturesque marina offering outdoor adventures such as boat rentals and dining with waterfront views. Experience the blend of adventure and beach vibes while enjoying the beautiful Sarasota Bay.

Things to do recommended for couples

For a romantic getaway in Siesta Key Village, indulge in the luxury of The Oaks Club, enjoy a captivating performance at Beatrice Friedman Symphony Center, or have fun at Evie's Golf Center for a playful mini-golf experience. Each offers a unique vibe for couples to cherish together.

Things to do recommended for families

Experience the excitement at Ed Smith Stadium, just 6 miles from Siesta Key Village, where sports vibes come alive. For a day of wellness and relaxation, visit the Robert L. Taylor Community Complex, located 7 miles away, perfect for family bonding and recreational activities.

Things to do recommended for groups

Experience the arts at Van Wezel Performing Arts Hall, just 5 miles away, or embark on an adventure at Sarasota BayWalk, 4 miles away. For some retail therapy, visit Gulf Gate Mall, located 3 miles from Siesta Key Village, perfect for family fun and entertainment.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, or pets, or if you're considering an extended stay, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Siesta Key Village with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Siesta Key Village with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private 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 vacation isn’t truly enjoyable without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure 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 offering special rates 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 options like a parking spot, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Siesta Key Village

Siesta Key Village is a charming destination perfect for a beach-themed vacation, offering a delightful blend of relaxation and family-friendly activities. Explore the stunning Siesta Key Beach, known for its powdery white sand and vibrant atmosphere. Enjoy the tropical scenery and friendly locals as you unwind in vacation homes or indulge in the island getaway experience. With beautiful beaches and a welcoming vibe, Siesta Key Village is an ideal spot for your perfect beach getaway.

  • Siesta Key: Siesta Key is a picturesque barrier island known for its stunning white sandy beaches and vibrant village atmosphere. Siesta Key Village serves as the heart of the island, where visitors can enjoy a range of family-friendly activities, from beach outings to shopping and dining experiences. This island offers a perfect blend of outdoor adventures and relaxation, with attractions like the famous Siesta Beach, which is often ranked among the best in the U.S. The area is dotted with charming shops, restaurants, and recreational areas, making it an ideal destination for families and beach lovers alike.
  • Sarasota: Located just 5 miles from Siesta Key Village, Sarasota is a bustling city that offers a more urban experience while still being close to the beach. Visitors flock to Sarasota for its cultural attractions, including art galleries, theaters, and a vibrant downtown area filled with shopping malls and dining options. The city's beautiful beaches, such as Lido Key Beach and Siesta Key Beach, provide a perfect escape for families looking to enjoy sun and sand. Sarasota’s waterfront parks and cultural venues, like the Ringling Museum of Art, make it a well-rounded destination for travelers.
  • Lido Key: A charming island located 3 miles from Siesta Key Village, Lido Key is known for its serene beaches and family-friendly atmosphere. Visitors are drawn to Lido Key for its stunning coastal scenery and recreational areas. The island features beautiful parks and easy access to shopping centers, providing a blend of relaxation and leisure. Lido Beach is a popular spot for families to enjoy sunbathing and water activities, while the nearby urban parks offer opportunities for picnicking and outdoor fun, making it a perfect addition to your Siesta Key vacation itinerary.

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.

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 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 SunnyModerately HighSlightly 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 a breeze

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the planner definitely has its perks. By becoming a member of our travel rewards program, One Key, you can immediately access exclusive savings and earn OneKeyCash on eligible bookings. Sign up today to start enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for planning new adventures, refining existing itineraries, or managing your reservations. All the properties you've saved or booked are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/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 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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