Siesta Key holiday homes

We found 7,171 holiday rentals — enter your dates for availability
Discover a selection of 401 homes, 73 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:5 Feb - 12 Feb

Image gallery for Rare private beachfront estate on the Gulf.

Pool
10 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)

Rare private beachfront estate on the Gulf.

Nokomis

8% off
Price is NZ$47,541
for 7 nights, 1 home
NZ$6,792 per night
includes taxes & fees
Rare private beachfront estate on the Gulf.

Find spaces that suit your style

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Why visit Siesta Key

  • Stunning Beaches: Relax on the pristine, family-friendly beaches, especially the renowned Siesta Key Beach with its soft, white sands.
  • Vibrant Village: Explore the lively Siesta Key Village, filled with charming shops, restaurants, and a welcoming atmosphere.
  • Outdoor Activities: Enjoy a variety of outdoor adventures, from water sports to nature walks in the scenic parks and marina.
  • Relaxed Atmosphere: Experience the laid-back vibe perfect for leisurely days under the sun, ideal for families and couples alike.
  • Cultural Experiences: Immerse yourself in the local culture through events, art, and community gatherings throughout the area.

Top attractions in and around Siesta Key

Siesta Key is a stunning coastal city perfect for a family or outdoor holiday. Enjoy its beautiful beaches, urban parks, and marina that offer a blend of relaxation and a touch of city vibes. Whether you're exploring nature or taking in the local culture, Siesta Key provides an ideal backdrop for creating memorable experiences. This beachside haven is sure to charm every visitor with its unique blend of leisure and excitement.

  • Siesta Key Beach: Renowned for its powdery white sands and crystal-clear waters, Siesta Key Beach offers a relaxed atmosphere perfect for sunbathing, swimming, and beach games. The vibrant sunsets are a must-see.
  • St. Armands Circle: A charming shopping and dining district featuring unique boutiques, art galleries, and delightful eateries, St. Armands Circle presents a bustling city vibe where you can enjoy leisurely strolls.
  • Lido Beach: Known for its serene setting and natural beauty, Lido Beach provides a tranquil escape with opportunities for swimming, picnicking, and enjoying stunning coastal views.

Things to do recommended for couples

Discover Siesta Key’s charm with a sunset sail, hand in hand along pristine beaches, and a cosy seaside dinner. Enjoy the local flavours and vibrant arts scene, making every moment a treasure for you both.

Things to do recommended for families

Families can enjoy a variety of kid-friendly experiences in Siesta Key, such as building sandcastles on the famous Siesta Beach and exploring local marine life at the vibrant tide pools, perfect for a sun-soaked family adventure.

Things to do recommended for groups

Experience adventure on the TreeUmph. Adventure Course, a zipline and ropes course located 29km from Siesta Key. Perfect for group travellers seeking an outdoor thrill and local flavour in their holiday adventures.

*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

When planning your trip, whether you’re travelling with a group, family, pets, or seeking longer stays, be sure to use the appropriate filters that align with your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Siesta Key with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group get-togethers. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Siesta Key with young kids: Travelling with young kids can be quite a task. It's important to prioritise their comfort and safety, as well as having access to suitable amenities like 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: For many, a family holiday isn’t complete without including their furry companion. If this describes you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Siesta Key: If you're in search of 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 options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Siesta Key

Siesta Key offers a relaxing tropical escape with its pristine, family-friendly beaches. Enjoy the golden sands of Siesta Key Beach and explore the vibrant Siesta Key Village, where the atmosphere is friendly and laid-back. Stroll along the picturesque Siesta Beach and savour the island’s unique charm, perfect for outdoor adventures and leisurely days under the sun.

  • Sarasota: Located approximately 8km from Siesta Key, Sarasota is a vibrant city known for its beautiful beaches and family-friendly atmosphere. Visitors can enjoy a blend of urban and coastal experiences, with plenty of shopping centres and recreational areas to explore. The city's cultural scene is rich, featuring galleries, theatres, and local markets. Notable landmarks include the stunning beaches that cater to families and beachgoers alike, as well as charming town neighbourhoods that offer a taste of local life. Sarasota is perfect for those looking to combine beach relaxation with urban adventures.
  • Siesta Key Village: Siesta Key Village is a charming neighbourhood located within Siesta Key, offering a delightful beach-themed experience. This area is known for its relaxed vibe, making it an ideal spot for families and visitors seeking leisure. With a variety of recreational areas, shopping centres, and local eateries, Siesta Key Village is a hub of activity. The famous Siesta Beach, renowned for its soft white sands, is just a stone's throw away, providing ample opportunity for sunbathing and water sports. The village encapsulates the spirit of coastal living, making it a must-visit destination.
  • Lido Key: Situated about 5km from Siesta Key, Lido Key is a picturesque island that offers a unique blend of beach and urban experiences. Known for its pristine beaches and family-friendly atmosphere, visitors can indulge in shopping and recreational activities within the area. Lido Key features beautiful urban parks and beach access, perfect for picnics and outdoor fun. The scenic views and relaxed pace of life make Lido Key an excellent choice for families and those looking to unwind while still having access to city 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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 a breeze

Looking to cut costs on your next getaway? Try being flexible with your travel dates, as prices can vary. Also, booking a longer stay might help you save significantly. To find the ideal Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's clever Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or keep track of your travel arrangements. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: 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)
  • University Park Country Club (10.5 mi / 16.9 km)
  • Premier Sports Campus at Lakewood Ranch (15.7 mi / 25.2 km)
  • Pelican Pointe Golf and Country Club (16.6 mi / 26.8 km)
  • Links on Longboat (4.3 mi / 6.9 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 best area to stay in Siesta Key when booking a holiday rental?
When considering a holiday rental in Siesta Key, Florida, the area around Siesta Beach is often regarded as one of the best. Known for its powdery white sands and crystal-clear waters, Siesta Beach is a top attraction that draws visitors from all over. The beachfront boasts a lively option, superb for sunbathing, swimming, and enjoying the stunning sunsets.

Another excellent neighbourhood to explore is the Village of Siesta Key. This charming area offers a delightful mix of shops, restaurants, and cafes, making it a great spot for those who appreciate a vibrant local culture. Here, you can indulge in delicious seafood at one of the eateries or browse unique boutiques. The village also hosts various events throughout the year, adding to its appeal.

In terms of holiday rentals, Siesta Key offers a diverse selection of properties, from beachfront condos to cosy cottages. This variety ensures that visitors can find accommodations that suit their needs, whether they are seeking a romantic getaway or a family-friendly environment.
Where are the best areas for renting a beach house in Siesta Key?
For renting a beach house in Siesta Key, the most sought-after areas are along the stunning shoreline near Siesta Beach, renowned for its powdery white sand and clear turquoise waters. Properties in this vicinity often offer a range of amenities, including private pools, outdoor patios for al fresco dining, and direct beach access, making them great for families and groups looking to enjoy the sun and surf. Many rentals also come with modern kitchens and spacious living areas, allowing for comfortable stays.

Another excellent option is the Crescent Beach area, which features a more tranquil atmosphere while still being close to local shops and restaurants. Here, beach houses often include luxurious amenities such as hot tubs, balconies with sea views, and easy beach access. The serene environment is ideal for those looking to unwind while enjoying the natural beauty of the coastline.

Near the village area of Siesta Key, visitors can find charming bungalows and condos that offer a vibrant local experience. These properties are typically equipped with essentials like Wi-Fi, laundry facilities, and communal pools, providing a convenient base for exploring the nearby boutiques and eateries. The proximity to the lively option of the village, with its seasonal events and nightlife, makes this an attractive option for those wanting a mix of relaxation and social activities. Find your rental near the beach in Siesta Key.
What is the most popular type of holiday rental accomodation in Siesta Key?
In Siesta Key, condos are the most popular type of holiday rental, with approximately 8,936 available throughout the area. These condos are typically located close to the stunning Siesta Key Beach and provide a range of amenities, including fully equipped kitchens, spacious living areas, and access to community pools. Many also feature private balconies or patios, superb for enjoying the warm Florida weather and picturesque views.

For those seeking more space, there are around 2,820 holiday houses available, which often come with multiple bedrooms, private gardens, and outdoor seating areas, making them ideal for families or larger groups. Additionally, there are around 808 apartments and 760 villas, offering further options for travellers looking for a comfortable stay.
Are there any family house rentals in Siesta Key?
In Siesta Key, there are numerous family-friendly house rentals available, with around 2,158 options for visitors to choose from. This vibrant locale is known for its stunning beaches and family-friendly atmosphere, making it an ideal destination for groups.

Properties in Siesta Key often feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces superb for children to play. Many homes also provide amenities such as private pools, barbecue grills, and access to beach gear, ensuring a comfortable and enjoyable stay.

Families can explore nearby attractions, including the beautiful Siesta Beach, which offers soft white sands and gentle waves, making it superb for little ones. The area is also close to various parks and recreational facilities, providing ample opportunities for outdoor activities. See all family-friendly rentals in Siesta Key.
Can I rent a holiday home with a pool or hot tub in Siesta Key?
In Siesta Key, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 2,935 options to choose from. This picturesque island is renowned for its stunning beaches and vibrant setting, making it an ideal destination for those seeking a relaxing getaway.

Travellers can expect a variety of amenities in these rentals, including private swimming pools, soothing hot tubs, and spacious outdoor areas for sunbathing or barbecuing. Many properties also come equipped with fully furnished kitchens, making it easy to prepare meals during your stay. Additionally, some rentals may offer proximity to the beach, ensuring that guests can easily enjoy the soft sands and clear waters that Siesta Key is famous for. Find your rental in Siesta Key with a pool or a hot tub.
Are there pet-friendly house rentals in Siesta Key?
In Siesta Key, there are numerous pet-friendly house rentals available, with over 500 options to choose from. This charming coastal destination is known for its stunning white sandy beaches and vibrant local culture. Many of the holiday homes come equipped with modern amenities such as private pools, outdoor grilling areas, and spacious living spaces, superb for families or groups travelling with pets.

The area around Siesta Beach is particularly popular, offering easy access to the beach where pets are often welcome during certain hours. Additionally, the nearby Siesta Key Village features various pet-friendly cafes and shops, making it convenient for travellers to enjoy the local atmosphere with their furry companions.

For those interested in outdoor activities, the nearby parks and nature reserves provide ample opportunities for walking and exploring with pets, enhancing the overall experience of a holiday in this beautiful part of Florida. See all pet-friendly rentals in Siesta Key.
Are there any remote work holiday rentals in Siesta Key?
In Siesta Key, Florida, there are numerous remote work holiday rentals available, with around 12,576 properties suiting those looking to combine work and leisure. This picturesque destination is renowned for its stunning beaches and vibrant setting, making it an ideal spot for remote workers. Many of these rentals come equipped with essential amenities such as free Wi-Fi, designated workspaces with desk and chair setups, and comfortable living areas that allow for a productive yet relaxing environment.

Travellers can expect a variety of property types, including beachfront condos and spacious homes, often featuring outdoor spaces to unwind after a day of work. The area is close to points of interest like Siesta Beach, which is famous for its powdery white sands, and the lively Siesta Key Village, where shops and dining options abound. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Siesta Key?
In Siesta Key, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and onsite parking for convenience. Many rentals also feature coffee and tea makers, great for those who enjoy a warm beverage in the morning. Additionally, the proximity to the beach is a key attraction, with many properties located just a short walk away from the sandy shores. For those looking to relax, shared pools are commonly available, providing a refreshing option for cooling off after a day in the sun.
When is the best time to visit Siesta Key for a holiday rental?
The best time to visit Siesta Key for a holiday rental is during the peak season, which runs from January to March. This popular period attracts visitors seeking sunny escapes to enjoy the stunning beaches, vibrant nightlife, and a number of outdoor activities. January, in particular, is a favourite month, offering mild temperatures averaging around 15 to 24 degrees Celsius, superb for sunbathing and water sports.

During these months, Siesta Key comes alive with tourists, creating a lively option ideal for socialising and engaging in local events. The beautiful white sand beaches are superb for relaxing, while activities such as kayaking, paddleboarding, and beach volleyball abound. The warm winter climate makes it a comfortable choice for both outdoor adventures and leisurely sightseeing.

If you're looking for a more budget-friendly option, consider visiting in November. This month often sees fewer crowds, allowing you to enjoy the tranquil beauty of Siesta Key at a more relaxed pace. You can still experience the natural charm of the area, with many attractions available and pleasant weather.
What are the top attractions in Siesta Key?
In Siesta Key, visitors can enjoy a variety of attractions that highlight the area's natural beauty and vibrant setting. The renowned Siesta Key Beach is known for its powdery white sand and crystal-clear waters, making it a prime spot for sunbathing and swimming. Nearby, the Siesta Key Village offers a charming area filled with shops, restaurants, and nightlife, great for leisurely strolls and dining experiences.

For those interested in nature, the nearby Turtle Beach provides a quieter alternative with opportunities for kayaking and fishing. The scenic spots along the coastline are ideal for sunset views and enjoying the tranquil surroundings.

Additionally, the area is great for water sports, with options for paddleboarding and parasailing available at various points along the beaches.
Are all fees included in the Siesta Key holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Siesta Key holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Siesta Key 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 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.
Are there any discounts for Siesta Key holiday homes?
You can find great discounts on holiday homes in Siesta Key on Bookabach, 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.
Can I change or cancel my Siesta Key holiday home booking on Bookabach?
To find Siesta Key holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Siesta Key?
A long-stay holiday home in Siesta Key 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Siesta Key holiday home?
Book your Siesta Key holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Siesta Key?
Prices for holiday homes in Siesta Key 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Siesta Key to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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