Siesta Key Village holiday lettings

We found 1,120 holiday rentals — enter your dates for availability

Discover a selection of 121 homes, 36 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:29 May - 5 Jun

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 £4,833
for 7 nights, 1 home
£690 per night
includes taxes & fees
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

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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

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?
The best time to visit Siesta Key Village for a holiday rental is during the peak season from January to March. This period attracts sun-seekers and beach lovers keen to enjoy the warm, inviting weather, with temperatures typically ranging from 15 to 25 degrees Celsius. The beaches are vibrant, and the charming village buzzes with activity, offering a great blend of relaxation and fun.

January, in particular, is a fantastic time to visit as it brings mild temperatures and a lively option. The stunning white sands of Siesta Key Beach are ideal for sunbathing, swimming, and various water sports, while the nearby shops and restaurants provide plenty of opportunities for exploration and indulgence.

If you're looking for a more budget-friendly option, consider planning your trip in November. While this month is outside the peak tourist season, it still offers pleasant weather and a more tranquil experience, allowing you to enjoy the natural beauty and local charm without the crowds.
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, 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 famous Siesta Key Beach, known for its powdery white sand and crystal-clear waters, is a major draw, great for sunbathing, swimming, and beach volleyball. Close to the beach, the village itself offers a delightful selection of shops, restaurants, and cafes, creating a lively option for leisurely strolls.

The Siesta Key Village frequently hosts local events, such as art fairs and live music performances, providing a vibrant community experience. Additionally, the nearby Point of Rocks on the southern end of Siesta Key Beach is a popular spot for snorkelling, where visitors can explore marine life in the shallows. For those interested in outdoor activities, the village's proximity to the scenic Legacy Trail offers opportunities for biking and walking through beautiful landscapes.
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 cabin or a beach house, 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 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.
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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

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