Siesta Key holiday lettings

We found 6,738 holiday rentals — enter your dates for availability

Discover a selection of 396 homes, 85 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:22 May - 29 May

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Pool
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Sarasota

8% off
Price is £11,154
for 7 nights, 1 villa
£1,593 per night
includes taxes & fees
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Find spaces that suit your style

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.

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.

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

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.

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)
  • 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 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.
How much does it cost to rent a holiday home in Siesta Key?
Prices for holiday rentals 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 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 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 holiday house rentals?
You can find great discounts on house rentals in Siesta Key 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.
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.
Can I find long-stay holiday rentals in Siesta Key?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Siesta Key holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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.
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.
How early should I book a Siesta Key holiday rental?
Book your Siesta Key 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?
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.
Can I change or cancel my Siesta Key home rental booking on Vrbo?
To find Siesta Key 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 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.

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