Siesta Key holiday homes

We found 6,441 holiday rentals — enter your dates for availability

Discover a selection of 808 homes, 243 apartments and other holiday rentals in Siesta Key that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as a garden and pool. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Siesta Key

Showing deals for:12 Dec - 19 Dec
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Why visit Siesta Key

  • Gorgeous Beaches: Relax on Siesta Key Beach, famous for its soft, powdery white sands and stunning sunsets.
  • Family-Friendly Activities: Enjoy a variety of outdoor activities suitable for all ages, from beach games to water sports.
  • Charming Neighbourhoods: Explore the friendly communities of South Siesta Key, filled with local charm and breathtaking views.
  • Marina Fun: Take advantage of the marina for boating, fishing, and other water-based adventures.
  • Urban Parks: Discover beautifully maintained parks offering spaces for picnics, walking, and enjoying nature.

Top attractions in and around Siesta Key

Siesta Key is the perfect destination for a beach holiday, offering family-friendly outdoor activities and urban parks. You can explore the stunning Siesta Beach, known for its powdery white sand, and enjoy the marina's offerings. Don't miss the attractions around Siesta Key, ideal for those seeking a mix of city and coastal experiences. Whether you're soaking up the sun or enjoying family outings, Siesta Key has something for everyone.

  • Siesta Key Beach: Renowned for its powdery white sand and stunning sunsets, Siesta Key Beach is perfect for sunbathing, swimming, and beach games, offering a relaxed tropical vibe.
  • St. Armands Circle: A lively shopping and dining destination, St. Armands Circle features unique boutiques and gourmet eateries, making it a vibrant place to explore and enjoy city life.
  • Lido Beach: Known for its tranquil atmosphere, Lido Beach offers a less crowded experience with beautiful views, ideal for a peaceful day by the water.

Things to do recommended for couples

Looking for a romantic getaway in Siesta Key? Enjoy the luxury vibes at The Oaks Club, catch a performance at the Beatrice Friedman Symphony Center, or have some fun at Evie's Golf Center. Each offers a unique experience for couples seeking adventure and relaxation.

Things to do recommended for families

Families can explore the wellness vibes at Robert L. Taylor Community Complex, only 11.3km from Siesta Key, or catch a game at Ed Smith Stadium, a sports venue located 9.7km away. Both offer fantastic experiences for the whole family.

Things to do recommended for groups

Experience the vibrant culture at the Van Wezel Performing Arts Hall, only 8.0km from Siesta Key. For a bit of adventure, hike the scenic Sarasota BayWalk, 6.4km away. Don’t miss the Siesta Key Farmers Market for a taste of local business and family vibes right in the area.

*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 in Siesta Key

If you're heading off on an adventure with friends, family, pets, or planning an extended getaway, it's important to prioritise your preferences when filtering options. Here are some helpful tips for booking on Vrbo.

  • Traveling to Siesta Key with a group: Think about how many bedrooms you’ll require, as well as features like a fully equipped kitchen or outdoor areas for socialising with your group. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Siesta Key with young kids: Taking a trip with young kids can be quite a task. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, thinking about how close you are to family-friendly activities is a wise choice.
  • Taking your pets with you to Siesta Key: For many families, a holiday isn’t truly memorable unless their furry companion is along for the ride. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that your whole family feels at home.
  • Planning for a long term stay visiting Siesta Key: If you're in search of 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 as well.

Where to stay in and around Siesta Key

Siesta Key, a stunning island destination in Florida, offers a tropical escape perfect for families and beach lovers. With its powdery white sands and inviting atmosphere, Siesta Key Beach is a must-visit. Explore the friendly neighbourhoods around South Siesta Key for a taste of local charm and breathtaking scenery. Whether you’re after relaxation or outdoor adventures, you’ll find a slice of paradise waiting for you in this beautiful region.

  • Sarasota: Situated a mere 8.0km from Siesta Key, Sarasota is a vibrant city that seamlessly blends beachside charm with urban sophistication. Visitors flock here for its family-friendly atmosphere, diverse shopping options, and cultural experiences. Explore the local shopping malls and centres, or unwind on the stunning beaches that define this coastal haven. Not to be missed are the family beaches and urban parks, perfect for a day out with the kids or a leisurely stroll amidst nature.
  • Siesta Key Village: Nestled within Siesta Key, Siesta Key Village is a delightful neighbourhood that embodies the essence of beach life. Known for its friendly vibe, the village offers a mix of recreational areas and shopping venues, making it an ideal spot for families. Visitors can enjoy the sun-kissed beaches or take a break in the local urban parks. The village is a fantastic starting point for those looking to experience the laid-back lifestyle of Siesta Key while having easy access to various activities.
  • Lido Key: Located just 4.8km from Siesta Key, Lido Key is a picturesque island destination that attracts beach lovers and families alike. This charming locale features a range of recreational areas and shopping centres that cater to every need. With its pristine beaches and inviting urban parks, Lido Key offers a perfect blend of relaxation and adventure. It's an excellent choice for those looking to explore the stunning coastal scenery while enjoying the local attractions.

Best time to go to Siesta Key

If you're planning a trip to Siesta Key, it's a good idea to check both the weather and property rates. The warmest month is August.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyModerately High
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately High
April73.4°F (23.0°C)Light RainMostly SunnyAverage
May77.7°F (25.4°C)Light RainMostly SunnyAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverage
July82.9°F (28.3°C)Light RainMostly SunnyModerately High
August83.3°F (28.5°C)Light RainMostly SunnyAverage
September81.5°F (27.5°C)Light RainMostly SunnyAverage
October77.2°F (25.1°C)Light RainMostly SunnyModerately Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyModerately Low
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyModerately Low

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy space for you to plan new adventures, continue from where you last saved, or manage your travel arrangements. You can easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Why people love visiting lively Siesta Key

Enjoy the live music and other features of Siesta Key. Well known for its beaches, seaside and sporting events, this relaxing city won't disappoint. Siesta Key Beach and Lido Beach are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Siesta Key

Are you hoping to discover top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Siesta Key a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mote Marine Laboratory & Aquarium (4.1 mi / 6.6 km)
  • Sarasota Jungle Gardens (6.4 mi / 10.3 km)
  • Premier Sports Campus at Lakewood Ranch (15.7 mi / 25.2 km)
  • Sarasota National Golf Course (20.7 mi / 33.4 km)
  • Islandside Golf Course at Longboat Key Club (4.3 mi / 6.9 km)
  • Harborside Golf Course at Longboat Key Club (4.3 mi / 7 km)

Exploring the beaches and other natural features in Siesta Key

Travellers enjoy Siesta Key for its sunsets, seaside and tropical setting. Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Siesta Key is a great spot to appreciate mother nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Siesta Key Beach (0.9 mi / 1.5 km)
  • Lido Beach (2.4 mi / 3.9 km)
  • Crescent Beach (2.3 mi / 3.8 km)
  • Point of Rocks (2.7 mi / 4.3 km)
  • Marie Selby Botanical Gardens (3.9 mi / 6.2 km)
  • Turtle Beach (4.4 mi / 7.1 km)

Seasonal weather in Siesta Key

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 28°C.

Transport to and around Siesta Key

The nearest airport is in Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), located 7.8 mi (12.5 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Siesta Key?
The most in-demand types of holiday homes in Siesta Key are condos. Want something different? Bookabach has plenty of options to match the needs of our guests, so you'll see holiday properties in all sizes, and for all budgets. The perfect fit is waiting for you — discover yours today.
How much does it cost to rent a holiday home in Siesta Key?
The average price for a holiday home in Siesta Key is determined by a number of factors, such as length of stay, property type and season. Whether you're thinking about a sprawling villa with space for the whole family or a cosy cabin for just you and the kids, just enter your travel dates to see stays that offer great value.
How much does it cost to rent a beach house in Siesta Key?
Prices for beach houses in Siesta Key can vary depending on the size and type of the property and time of year you're travelling. All you have to do is enter your travel dates into Bookabach and how many guests to see available options and prices. From there you can use the filters to narrow your search by ratings, amenities and more.
What are popular home amenities in Siesta Key?
An electric car charging station, tennis and a garden top the list of most popular home amenities in Siesta Key. Whether you plan to travel solo, with your spouse or a group of friends, Bookabach can help you find a holiday home that fits your style with all the features you need.
What are the top attractions for families in Siesta Key?
Keep your kids busy at these leading family-friendly attractions in Siesta Key:

  • Siesta Key Beach
  • Lido Beach
  • Turtle Beach

Can I find two-bedroom holiday homes in Siesta Key?
Gather your loved ones and enjoy a relaxing escape in one of the 1,076 two-bedroom holiday properties Siesta Key has to offer.
Are there holiday homes with WiFi in Siesta Key?
Whether you'd like to keep up with the headlines, write a few emails or surf social media, there are 403 holiday homes with WiFi in Siesta Key. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How old do you have to be to rent a holiday home in Siesta Key?
We recommend checking with the Siesta Key holiday home you're looking at on Bookabach as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Siesta Key for?
It really depends on the Siesta Key property. To see all available options offering extended stays, simply type your travel dates and number of people into Bookabach's search page. You can look forward to having the entire place to yourself, along with the comforts of home like air conditioning, a fully-equipped kitchen and outdoor spaces to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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