Siesta Key Village vacation rentals

We found 1,118 vacation rentals — enter your dates for availability

Discover a selection of 123 homes, 37 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:May 15 - May 22

Image gallery for Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

Open, sunlit living space with designer furnishings and seamless entertaining.
10 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)

Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

Siesta Key

7% off
Price is $877
$6,142 for 7 nights
All fees included
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

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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 type of rental accommodation, with around 160 available. These houses are often situated near the beach and provide ample space for families or larger groups, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas like patios or decks for enjoying the tropical weather. Condos follow closely behind, with about 81 options that typically offer amenities such as pools, fitness centers, and close proximity to local shops and dining. Apartments, numbering around 45, provide a more compact and convenient choice, often including kitchen facilities and easy access to the village's vibrant setting.
Are there any beach house rentals in Siesta Key Village?
In Siesta Key Village, there are approximately 667 beach house rentals available, suiting a variety of vacation needs. These properties are predominantly located near the picturesque Siesta Beach, known for its powdery white sand and vibrant setting. Most beach houses offer amenities such as fully equipped kitchens, spacious living areas, and outdoor patios or decks, ideal for enjoying the coastal breeze. Many properties also include features like private pools, BBQ grills, and direct beach access, making them superb for families or groups looking to relax and make the most of their beach vacation.
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, popular vacation rental amenities include fully equipped kitchens, which allow guests to prepare meals and enjoy dining in a home-like setting. Many rentals also offer onsite parking for convenience, making it easier for travelers with vehicles. Additionally, most properties feature coffee and tea makers, great for enjoying a warm beverage in the morning. Outdoor spaces such as decks or patios are common, providing a nice area to relax and soak in the Florida sunshine. Many accommodations also include sofa beds, offering extra sleeping arrangements for larger groups or families.
Can I find family house rentals in Siesta Key Village?
In Siesta Key Village, there are around 225 family-friendly house rentals available, making it an excellent choice for families seeking a getaway. This vibrant area is known for its stunning beaches and a lively option, great for group gatherings. Many of these homes feature spacious living areas, full kitchens ideal for preparing family meals, and outdoor patios where children can play and adults can relax.

Visitors will appreciate the proximity to local attractions such as Siesta Beach, renowned for its soft quartz sand, and the charming shops and restaurants that line the village. The amenities offered often include essentials like Wi-Fi, air conditioning, and sometimes even private pools or game rooms, ensuring a comfortable stay for everyone.
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 214 options boasting pools and 49 offering hot tubs. This charming village, known for its stunning beaches and vibrant setting, provides a variety of rental properties, including beach cottages and larger family homes. Travelers can expect amenities such as private pools, relaxing hot tubs, outdoor dining areas, and fully equipped kitchens, great for enjoying the beautiful Florida weather.
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.
Can I book pet-friendly vacation rentals in Siesta Key Village?
Yes, you can book pet-friendly vacation rentals in Siesta Key Village, with a variety of options available for travelers with pets. This charming area offers a range of vacation rentals, including beachfront condos and cozy cottages, many of which come equipped with amenities such as full kitchens, outdoor seating areas, and easy access to the beach.

Siesta Key Village is known for its beautiful beaches and vibrant setting, making it an ideal destination for pet owners. The nearby Siesta Key Beach is not only renowned for its soft, white sands but also allows pets on a leash at certain times of the day, providing an excellent opportunity for you and your furry friend to enjoy the sun and surf together.

Additionally, the village boasts pet-friendly dining options, allowing you to relax and enjoy meals with your pet by your side.
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?
The most popular time to visit Siesta Key Village is from January to March, when travelers flock to this sun-soaked destination to escape colder climates. This peak season offers ideal conditions for outdoor activities, with average temperatures ranging from the upper 50s to mid-70s Fahrenheit, great for beach lounging, water sports, and exploring the vibrant local scene.

During these months, the village buzzes with life, featuring lively events, delicious dining options, and beautiful sunsets along the famous Siesta Key Beach. The warm weather allows for a plethora of activities, from paddleboarding and kayaking to enjoying leisurely strolls on the powdery white sand.

If you're looking for a more budget-friendly experience, consider visiting in November. While this month sees fewer crowds, it still boasts pleasant temperatures and a charming atmosphere. You can enjoy quieter beaches and local attractions without the hustle and bustle of peak season, making it a great time for relaxation and exploration.

Ultimately, your ideal time to visit Siesta Key Village hinges on whether you prefer the vibrant energy of winter travelers or the peaceful charm of the shoulder months.
Are there any remote work vacation rentals in Siesta Key Village?
In Siesta Key Village, Florida, travelers looking for remote work vacation rentals will find a robust selection, with approximately 278 options available. The village is known for its stunning beaches and vibrant setting, making it an appealing destination for those combining work and leisure. Many of these rentals come equipped with essential amenities for remote work, including free Wi-Fi, dedicated desk spaces, and comfortable work areas within the units.

Staying in Siesta Key Village not only provides a conducive environment for productivity but also places you close to the area's attractions, such as the famous Siesta Beach and local shops, restaurants, and nightlife. After work hours, you can unwind by the beach or explore the charming streets filled with boutiques and eateries. 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, Florida, United States of America?
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 setting, featuring boutique shops, restaurants, and cafes that line the streets, making it great for leisurely strolls. The iconic Siesta Beach, renowned for its powdery white sand and clear azure waters, is just a short walk away, providing a stunning setting for sunbathing, swimming, and beach sports.

Nearby, the Siesta Key Crystal Classic, a renowned sand sculpting festival, draws crowds and showcases incredible artistry, typically held in November. The village also offers easy access to the beautiful Siesta Key Village Historic District, where visitors can explore local art galleries and cultural experiences. For outdoor enthusiasts, kayaking and paddleboarding in the nearby waters are popular activities, with rental options available right within the village.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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 Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

Frequently asked questions

Can I find a vacation rental in Siesta Key Village?
Yes, we offer vacation rentals close to top sights in Siesta Key Village, or you can go with a more secluded option if you want a relaxing place to stay. Visitors like the array of shops and popular beaches in Siesta Key Village. While you're here, grab a bite or have a drink at the top-notch restaurants and lively bars.
How many vacation rentals are there in Siesta Key Village?
Expedia has 125 vacation rentals for your stay in Siesta Key Village.
What's there to see and do in Siesta Key Village?
Enjoy the area's cultural attractions such as Nontando, or get outdoors into nature at a spot like Siesta Key Beach. While in the area, you can also visit popular places like Lido Beach and St. Armands Circle.
What's a vacation rental in Siesta Key Village like?
Vacation rentals are private accommodations you can stay in for a short or long stay in Siesta Key Village. Vacation rentals feature extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.

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