Siesta Key holiday rentals

We found 6,833 holiday rentals — enter your dates for availability
Discover a selection of 417 homes, 79 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:23 Oct - 30 Oct

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Why visit Siesta Key

  • Pristine Beaches: Enjoy the soft, white sands and crystal-clear waters of Siesta Key's stunning beaches, perfect for sunbathing and swimming.
  • Charming Village Atmosphere: Stroll through the vibrant village, where local culture and friendly ambience create a delightful experience.
  • Outdoor Activities: Engage in various outdoor pursuits, from leisurely walks in scenic parks to water sports at the marina.
  • Family-Friendly Environment: Siesta Key is ideal for families, offering ample spaces for picnics and outdoor fun.
  • Relaxing Accommodations: Choose from a variety of private holiday homes and cozy condos, ensuring a comfortable stay.

Popular types of accommodation in Siesta Key

You have decided on a trip to Siesta Key, and now comes the fun part – choosing your perfect accommodation. Enjoy your stay in Siesta Key with a selection of private holiday homes, cosy condos, and modern apartments. With siesta key rentals offering beach chairs and access to the famed siesta sands, your holiday experience is set for an unforgettable blend of relaxation and adventure right within this charming Florida city.

  • Private Holiday Homes: Enjoy the ultimate freedom with a self-contained private home, offering ample space and privacy for families or groups.
  • Condos: Experience a modern, stylish retreat in a well-appointed condo, perfect for a chic seaside escape.
  • Apartments: Settle into a comfortable apartment, ideal for a relaxed stay with essential amenities close at hand.
  • Villas: Indulge in a luxurious villa, providing elegant living spaces and an exclusive holiday experience.
  • Cottages: Embrace a quaint, cosy cottage for a charming and intimate seaside break.**

Top attractions in and around Siesta Key

Siesta Key offers an array of delightful attractions, boasting stunning beaches, scenic urban parks, and a charming marina. Ideal for family and outdoor holidays, the locale invites visitors to enjoy its sandy shores and inviting public spaces, perfect for leisurely strolls or picnics. With a vibrant city vibe, Siesta Key promises a memorable experience for all travellers looking to immerse themselves in its coastal charm.

  • Siesta Key Beach: Renowned for its powdery white sand and crystal-clear waters, Siesta Key Beach offers a laid-back atmosphere perfect for sunbathing, swimming, and beach volleyball. With stunning sunsets and vibrant beach vibes, it’s ideal for relaxation and family fun.
  • St. Armands Circle: This charming area features an array of boutique shops, cafes, and art galleries, creating a lively city vibe. Enjoy leisurely strolls while indulging in unique shopping and dining experiences amidst beautifully landscaped surroundings.
  • Marie Selby Botanical Gardens: A serene oasis, this botanical garden showcases diverse plant collections and stunning waterfront views. Perfect for families and couples, the gardens offer romantic spots and outdoor space for leisurely exploration and relaxation.

Things to do recommended for couples

Siesta Key offers idyllic moments for couples. Enjoy sunset walks on the powdery white sands, indulge in a candlelit dinner at a beachfront restaurant, or embark on a private kayak tour through serene waters. These experiences create lasting memories in this romantic Florida paradise.

Things to do recommended for families

Families visiting Siesta Key can enjoy the stunning Siesta Beach, known for its soft, white sand. Explore the vibrant marine life at the nearby Mote Marine Laboratory or embark on a dolphin-watching tour for an unforgettable experience.

Things to do recommended for groups

Group travellers in Siesta Key may venture to TreeUmph. Adventure Course, an exhilarating zipline and ropes course located 29km away, offering an adventurous outdoor experience.

*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

Whether you are travelling with a group, as a family, with your pets, or seeking longer stays, be sure to set the appropriate filters. Here are some Stayz booking pointers for you.

  • Traveling to Siesta Key with a group: Consider how many bedrooms you'll require, along with features like a fully equipped kitchen or an outdoor area for group gatherings. Fortunately, you can refine your search for all these and more on Stayz.
  • Traveling to Siesta Key with young kids: Travelling with young children can present its challenges. It’s essential to prioritise their comfort and safety, along with suitable amenities, such as a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Siesta Key: For many, a family holiday wouldn't feel complete without their furry companion by their side. If this resonates with you, explore Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably 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 place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Siesta Key

Siesta Key is a tropical island haven, perfect for family and outdoor holidays. Its pristine beach offers a relaxing retreat, while the vibrant village presents a taste of local culture and friendly ambience. Wander the charming streets to discover the laid-back spirit of this iconic Florida destination, where every moment is a celebration of sun, sand, and serene coastal beauty.

  • Sarasota: A vibrant city situated 8km from Siesta Key, Sarasota offers a mix of urban excitement and coastal relaxation. Visitors can enjoy a beachside ambience, family-friendly outings, and a city-themed experience. The area features various shopping centres and mall complexes, complemented by local attractions such as sandy beaches, family-oriented beach areas, and charming town neighbourhoods. It is an ideal destination for those seeking both leisure and cultural exploration.
  • Siesta Key Village: Nestled within the heart of Siesta Key, this neighbourhood offers a quintessential blend of beach life and urban convenience. Its close proximity to the pristine shoreline ensures a delightful beach and family experience, enhanced by nearby recreational areas and shopping centres. The village's local landmarks, including its expansive beach and welcoming town neighbourhoods, provide a picturesque setting for a memorable holiday outing.
  • Lido Key: An alluring island destination located 5km from Siesta Key, Lido Key captivates visitors with its inviting beach atmosphere and urban park settings. Here, travellers can indulge in a beachside retreat while enjoying access to various shopping centres and recreational facilities. The island's proximity to family-friendly beach areas and serene urban parks makes it a versatile choice for those desiring a blend of relaxation and city-themed adventures.

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. Peak season runs in January, March and July, while off-peak times, like October to December 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 SunnyModerately HighSlightly Low
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverageAverage
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 SunnyAverageSlightly 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 SunnyModerately LowAverage

Booking with Stayz is a breeze

If you're planning your next journey and want to save money, why not consider being flexible with your travel dates? Prices do tend to vary, so you might find a better deal. Moreover, opting for a longer stay can often result in significant savings. To locate the perfect Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz's Trip Board offers a user-friendly space to create new journeys, resume where you previously paused, or review and organise your plans. Here, you'll find properties you've either saved or booked, neatly categorised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

The information above was last updated:

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)
  • University Park Country Club (10.5 mi / 16.9 km)
  • Premier Sports Campus at Lakewood Ranch (15.7 mi / 25.2 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)
  • Venice Beach (14.1 mi / 22.7 km)
  • Coquina Beach (14.3 mi / 23.1 km)
  • Shell Beach (1.6 mi / 2.6 km)
  • Crescent Beach (2.3 mi / 3.8 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? Stayz 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 Stayz 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, Stayz 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 Stayz 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 Stayz 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 Stayz'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.