Siesta Key Village holiday lettings

We found 1,137 holiday rentals — enter your dates for availability
Discover a selection of 123 homes, 27 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:9 Oct - 16 Oct

Image gallery for Siesta Vista: private pool, beach block

Exterior
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Siesta Vista: private pool, beach block

Siesta Key

7% off
Price is £5,697
for 7 nights, 1 home
£814 per night
includes taxes & fees
Siesta Vista: private pool, beach block

Find spaces that suit your style

  • 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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Siesta Key Village

  • Pristine Beaches: Unwind on the soft, white sands of Siesta Key Beach, celebrated for its crystal-clear waters and ideal sunbathing conditions.
  • Charming Atmosphere: Stroll through the vibrant village filled with inviting shops and delightful eateries, perfect for leisurely exploration.
  • Family-Friendly Activities: Enjoy various outdoor activities at nearby parks, making it an excellent destination for families seeking fun together.
  • Local Hospitality: Experience the warmth and friendliness of local residents, enhancing your visit to this coastal gem.
  • Variety of Accommodations: Choose from private vacation homes, condos, and apartments for a comfortable stay tailored to every traveller.

Popular types of accommodation around Siesta Key Village

Welcome to Siesta Key Village, a charming neighbourhood in Siesta Key, Florida, where vibrant shops, delightful eateries, and stunning beaches come together to create an unforgettable experience. Discover the beauty of this coastal gem, with easy access to soft, white sands and crystal-clear waters. Popular accommodation options include houses, condos, and apartments, ensuring a perfect stay for every traveller. Siesta Key Village offers a unique blend of relaxation and adventure for all who visit.

  • Houses: The top choice for visitors in Siesta Key Village, offering spacious and comfortable accommodations for families or groups.
  • Condos: A popular option for those seeking modern amenities and proximity to local attractions, ideal for couples or small families.
  • Apartments: Perfect for a relaxed stay, providing a home-like atmosphere with essential facilities for self-catering.
  • Villas: Luxurious retreats that offer upscale living spaces with private pools and stunning views.
  • Cottages: Quaint and charming, these provide a delightful setting for a peaceful getaway by the beach.**

Top attractions near Siesta Key Village

Siesta Key Village, situated in Siesta Key, Florida, offers a delightful beachside experience perfect for families and urban explorers alike. Visitors can indulge in the sun-kissed beaches, explore the charming marina, and enjoy outdoor activities in the nearby urban park. With its vibrant atmosphere, the village provides a wonderful blend of relaxation and adventure, making it an ideal destination for those seeking a memorable vacation by the sea.

  • Siesta Key Beach: Renowned for its powdery white sands and turquoise waters, Siesta Key Beach offers a relaxing atmosphere perfect for sunbathing, swimming, and beach activities. Enjoy stunning sunsets and vibrant beach vibes that make it a perfect spot for unwinding.
  • Siesta Key Village: A charming hub filled with boutique shops, delightful dining options, and lively nightlife. The village's laid-back atmosphere invites you to explore local art, enjoy fresh seafood, and soak in the community spirit.
  • Siesta Key Farmers Market: Held weekly, this market showcases local produce, crafts, and artisanal goods, offering a taste of the region's flavours and a chance to mingle with locals.

Things to do recommended for couples

Seeking a romantic getaway in Siesta Key Village? Enjoy a sunset stroll along the pristine beach, indulge in a candlelit dinner at a waterfront restaurant, or take a couple’s kayak tour through the serene mangroves. Each moment promises to deepen your connection amidst stunning surroundings.

Things to do recommended for families

Families can explore the pristine beaches of Siesta Key, known for its soft, white sand. Enjoy kayaking in the calm waters or take a leisurely bike ride around the village, discovering local shops and eateries. Don't miss the vibrant sunset at Siesta Key Beach for a memorable end to your day.

Things to do recommended for groups

Groups visiting Siesta Key Village can experience the thrill of the TreeUmph. Adventure Course, an exciting zipline and ropes course located 29km away. This adventure hub offers a fantastic outdoor vibe, perfect for team bonding and exhilarating fun in the sun.

*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 planning a trip with a group, family, or pets, or if you're seeking longer accommodations, be sure to use the appropriate filters to prioritise your needs. Here are some helpful booking tips for 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. Thankfully, you can easily refine your search for all of this and more on Vrbo.
  • Traveling to Siesta Key Village with young kids: Travelling with young children can present some difficulties. It’s important to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. 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 holiday wouldn't be the same without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Siesta Key Village: If you’re searching for holiday rentals offering 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Siesta Key Village

Siesta Key Village, nestled in the heart of Siesta Key, Florida, offers a delightful blend of tropical charm and family-friendly experiences. Visitors can unwind on the pristine Siesta Key Beach, known for its powdery white sand and crystal-clear waters. The village itself is vibrant, filled with inviting shops, eateries, and a welcoming atmosphere perfect for leisurely strolls. Enjoy the laid-back vibe and immerse yourself in the warmth of local hospitality while exploring this idyllic coastal gem.

  • Sarasota: Located a mere 8km from Siesta Key Village, Sarasota is a vibrant city that combines urban charm with coastal allure. Known for its beautiful beaches and family-friendly atmosphere, visitors can indulge in a variety of activities, from shopping at the local mall to exploring delightful resorts. Sarasota's attractions include the stunning beaches, perfect for a family day out, and quaint neighbourhoods that offer a taste of local life. The city's cultural scene is also worth exploring, with art galleries and theatres enriching the experience.
  • Siesta Key: Siesta Key, an idyllic island community, is home to the famous Siesta Key Village. This charming location draws tourists seeking a beach, outdoor, and family experience. With its pristine beaches and recreational areas, Siesta Key is perfect for sunbathing, swimming, and engaging in water sports. The village itself offers a delightful mix of shopping options and family-friendly venues, making it an ideal spot for those looking to relax and enjoy the local atmosphere. The beauty of the island’s landscape adds to its appeal, ensuring a memorable visit.
  • Lido Key: Situated just 5km from Siesta Key Village, Lido Key is another picturesque island that attracts visitors with its beachside charm and city-like amenities. Known for its family-friendly environment, Lido Key offers a variety of recreational areas, shopping centres, and stunning beaches. Visitors can explore urban parks that provide a serene escape amidst the vibrant surroundings. Whether you’re lounging on the beach or enjoying the local shops, Lido Key promises a delightful combination of relaxation and entertainment.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 keen to save on your upcoming journey? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you may enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to organise results by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing arrangements, or review your bookings. Your saved or booked properties are neatly organised into categories: Potential, Upcoming, or Current Trips. To discover the Trip Boards, please 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.

More holiday ideas