Siesta Key holiday lettings

We found 6,434 holiday rentals — enter your dates for availability

Discover a selection of 810 homes, 231 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:10 Oct - 17 Oct
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Why visit Siesta Key

  • Stunning Beaches: Siesta Key Beach is famous for its soft, powdery white sands, perfect for sunbathing and swimming.
  • Charming Village: Explore Siesta Key Village, filled with delightful shops, restaurants, and a vibrant atmosphere.
  • Outdoor Activities: Enjoy a variety of water sports, hiking, and nature walks amidst beautiful surroundings.
  • Family-Friendly Atmosphere: Siesta Key is an ideal destination for families, offering numerous activities for all ages.
  • Diverse Accommodation: Choose from a range of private homes, condos, and apartments to suit your needs.

Popular types of accommodation in Siesta Key

You've chosen Siesta Key for your getaway, and now it's time to select the perfect accommodation. Discover the most sought-after options for your stay, including houses, condos, and apartments. With a range of Siesta Key holiday rentals available, you're sure to find the ideal spot that offers transparency, savings, and peace of mind. Explore our selection of holiday rentals in Siesta Key to make your trip truly memorable.

  • Houses: These are the top choice for visitors to Siesta Key, offering spacious and comfortable accommodations ideal for families, friends, or couples.
  • Condos: A popular option for those seeking a blend of convenience and luxury, condos provide fantastic amenities and proximity to the beach.
  • Apartments: A practical choice for solo travellers or small groups, apartments offer a home-like atmosphere for your stay.
  • Villas: These elegant properties deliver a touch of sophistication, perfect for those looking to indulge during their holiday.
  • Cottages: Quaint and charming, cottages provide a delightful escape with a homely feel, ideal for a relaxing retreat.**

Top attractions in and around Siesta Key

Siesta Key is the ideal destination for a beach holiday, perfect for families and outdoor enthusiasts alike. With a variety of attractions including stunning beaches, urban parks, and marinas, visitors can enjoy a delightful blend of nature and urban experiences. Whether you're seeking relaxation by the shore or engaging activities, Siesta Key offers something for everyone to enjoy during their stay.

  • Siesta Key Beach: Renowned for its powdery white sand, Siesta Key Beach offers a perfect retreat with crystal-clear waters, ideal for sunbathing and leisurely strolls along the shore, embodying quintessential beach vibes.
  • St. Armands Circle: A vibrant shopping and dining destination located 1.9km from Siesta Key, St. Armands Circle features a mix of upscale boutiques and delightful eateries, creating a lively city atmosphere for visitors to enjoy.
  • Point of Rocks: A unique natural formation within Siesta Key, Point of Rocks boasts stunning coastal scenery, making it an excellent spot for snorkelling and admiring marine life amidst peaceful outdoor surroundings.

Things to do recommended for couples

For a romantic getaway in Siesta Key, consider enjoying a concert at the Beatrice Friedman Symphony Center, indulging in luxury at The Oaks Club, or embarking on an adventurous round of mini golf at Evie's Golf Center. Each experience offers a unique charm for couples.

Things to do recommended for families

Families visiting Siesta Key can experience the thrill of a game at Ed Smith Stadium, located 3.7km away, or unwind at the Robert L. Taylor Community Complex, just 4.3km away, offering wellness and relaxation vibes for all ages.

Things to do recommended for groups

Experience the arts at the Van Wezel Performing Arts Hall, only 3.1km from Siesta Key, or explore the scenic Sarasota BayWalk hiking trail, located 2.5km away. For a bit of shopping, visit the Gulf Gate Mall, just 1.9km from Siesta Key, offering a vibrant atmosphere.

Booking with Vrbo is a breeze

Planning to save on your upcoming getaway? Being flexible with your travel dates can make a significant difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy substantial savings. To discover a Vrbo property that aligns with your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Where to stay in and around Siesta Key

Siesta Key, a stunning island destination in Florida, offers a perfect blend of relaxation and adventure. Explore the pristine Siesta Key Beach, renowned for its powdery white sands, or wander through the charming Siesta Key Village, brimming with delightful shops and eateries. With its tropical vibes and friendly atmosphere, Siesta Key is ideal for family getaways, ensuring a memorable experience surrounded by breathtaking scenery and a welcoming community.

  • Sarasota: Nestled a mere 3.1km from Siesta Key, Sarasota is a vibrant city that offers a delightful blend of beachside relaxation and urban sophistication. Known for its family-friendly atmosphere, visitors can indulge in shopping at the local mall and explore charming boutiques. The city's proximity to stunning beaches and family-centric activities makes it an ideal destination for those seeking both leisure and adventure. Don't miss the chance to visit the picturesque beaches and the welcoming neighbourhoods that define Sarasota's unique charm.
  • Siesta Key Village: Located within the stunning Siesta Key area, Siesta Key Village is a quaint neighbourhood perfect for tourists eager to enjoy a coastal retreat. Renowned for its beautiful beaches and family-friendly recreational areas, the Village offers a delightful mix of shopping and dining experiences. Stroll through the urban park or relax on the soft sands of the beach, where families can create lasting memories. The laid-back atmosphere and vibrant local scene make Siesta Key Village a must-visit for anyone looking to unwind.
  • Lido Key: Just 1.9km from Siesta Key, Lido Key is a scenic island that boasts pristine beaches and a family-oriented environment. Visitors can enjoy various activities, including shopping at local centres and exploring recreational areas. The island's natural beauty is complemented by its urban parks, making it a perfect spot for outdoor enthusiasts. Whether you're looking to bask in the sun on the beach or enjoy a leisurely stroll through the park, Lido Key offers an idyllic escape for families and beach lovers alike.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

What do I need to keep in mind when booking a vacation in 'Siesta Key

If you’re travelling with a group, family, or pets, or if you’re seeking extended stays, be sure to refine your search based on your key preferences. Here are some helpful tips for booking with Vrbo.

  • Traveling to Siesta Key with a group: Think about the number of bedrooms you require, as well as features like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Siesta Key with young kids: Embarking on a journey with young children can pose certain challenges. It’s essential to prioritise their comfort and safety, while also seeking out suitable amenities, like a private swimming pool. Additionally, it's wise to take into account your closeness to attractions that cater to families.
  • Taking your pets with you to Siesta Key: For many families, a getaway wouldn't feel complete without their beloved pet. If this resonates with you, we invite you to explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family, including your furry companions, feel comfortable and at home.
  • Planning for a long term stay visiting Siesta Key: If you're seeking holiday rentals with great offers 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new getaways, pick up where you last stopped, or review and arrange your travel plans. Properties you've previously saved or booked can now be found under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/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)
  • 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)
  • Stoneybrook Golf & Country Club (6.5 mi / 10.5 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)
  • Shell Beach (1.6 mi / 2.6 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)

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 rental accommodation in Siesta Key?
The most in-demand types of holiday rentals in Siesta Key are condos. Want something different? Vrbo 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 rental 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 Vrbo 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 rental amenities in Siesta Key?
An electric car charging station, tennis and a garden top the list of most popular rental amenities in Siesta Key. Whether you plan to travel solo, with your spouse or a group of friends, Vrbo can help you find a holiday rental 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 rentals 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 rentals 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 Vrbo and stay connected on your holiday.
How old do you have to be to rent a holiday rental in Siesta Key?
We recommend checking with the Siesta Key holiday home you're looking at on Vrbo as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental 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 Vrbo'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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