Villas and Holiday homes in Siesta Key, FL

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Siesta Key, FL holiday homes
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1858 Villa rentals in Siesta Key, FL

Best Siesta Key, FL villas and holiday homes with a pool

Among the 1858 accommodations in Siesta Key, FL, here are the 4 best villas and holiday homes with a pool

Siesta Beach Condo Rental With Direct Beach And Pool Access - Siesta Key, FL
9.5 2 reviews

Siesta Beach Condo Rental With Direct Beach And Pool Access

house, Siesta Key
This Siesta Key condo, an 8-minute walk from Crescent Beach and an 18-minute walk from Siesta Key Beach, is conveniently located within 18 kilometres of Sarasota attractions including the Ringling Museum.
This two-bedroom property boasts 72 square metres of floor space, comfortably accommodating up to 9 guests and featuring a fully equipped kitchen, private pool access, and cable TV.
Spacious 3br Siesta Key Condo With Private Beach Access - Siesta Key, FL
9.5 2 reviews

Spacious 3br Siesta Key Condo With Private Beach Access

house, Siesta Key
This 3-bedroom apartment in Siesta Key provides private beach access and is situated an 8-minute walk from Crescent Beach, 11.6 kilometres from Marina Jack Restaurant and Marina, and 17.7 kilometres from Sarasota International Convention Centre.
Boasting a floor area of 167 square metres, this family-friendly accommodation accommodates up to 11 guests with amenities including air conditioning, Wi-Fi, a swimming pool, a sauna, a terrace, a garden, and tennis courts, alongside 24-hour front desk service and on-site parking.
Charming Siesta Key Condo With Private Beach Access - Siesta Key, FL
9.5 4 reviews

Charming Siesta Key Condo With Private Beach Access

house, Siesta Key
This Siesta Key apartment is located a short walk from Crescent Beach, 17.7 kilometres from the John and Mable Ringling Museum of Art and 19.3 kilometres from the Sarasota International Convention Centre.
This 89 square metre apartment accommodates up to seven guests and features private beach access, an outdoor swimming pool, a sauna, a fitness centre, a tennis court, and on-site parking.
158 M² House ∙ 4 Bedrooms ∙ 8 Guests - Siesta Key, FL
10 8 reviews

158 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Siesta Key
This Siesta Key property is situated a 1.6km walk from Siesta Key Village and a 2.4km stroll from Siesta Key Beach, offering easy access to local amenities and the renowned beach.
The 157 square metre house comprises a main residence and a separate suite, sleeping up to eight guests, and boasts a private heated saltwater pool, hot tub, four HDTVs, and a private garage.

Best Siesta Key, FL villas and holiday homes with a kitchen

Heated Pool, Dock, Kayaks, 1-mile To Turtle Beach - Siesta Key, FL
9.8 40 reviews

Heated Pool, Dock, Kayaks, 1-mile To Turtle Beach

bungalow, Siesta Key
This bungalow is located on Heron Lagoon in Vamo, offering direct access to the lagoon and resort facilities, with the lagoon itself being a key natural attraction within 500 meters.
This family-friendly one-bedroom detached house sleeps up to three guests and features a private patio, complimentary kayaks for exploring Heron Lagoon, and a shared heated swimming pool and BBQ area.
Harbor Towers Ocean View Escape - Siesta Key, FL
No reviews

Harbor Towers Ocean View Escape

house, Siesta Key
This Siesta Key holiday home, 1.4 kilometres from Crescent Beach and 12 kilometres from the Ringling Museum of Art, offers convenient access to Siesta Key's pristine sands and cultural attractions.
The one-bedroom property sleeps eleven guests, boasting two bathrooms, a private pool, tennis court, free parking, a fully equipped kitchen including a dishwasher, and free Wi-Fi; enjoy on-site laundry facilities and stunning ocean views.
62 M² House ∙ 1 Bedroom ∙ 4 Guests - Siesta Key, FL
10 1 review

62 M² House ∙ 1 Bedroom ∙ 4 Guests

house, Siesta Key
This holiday cottage, Aloha Kai #60, is located directly on Crescent Beach, rated number one in the United States, and within the gated Aloha Kai resort on Siesta Key, offering walking distance to local restaurants and entertainment.
This 62-square-metre holiday home accommodates up to four guests with one bedroom and one bathroom, featuring air conditioning, a kitchen with a fridge, microwave oven, and dishwasher, a swimming pool, spa, parking, and complimentary beach toys and floats.
Crescent Royale Condominiums 306 - Siesta Key, FL
10 1 review

Crescent Royale Condominiums 306

house, Siesta Key
This holiday home in Crescent Royale Condominiums offers a prime Siesta Key location, just 400 metres from Siesta Key Beach, 17.7 kilometres from the Ringling Museum of Art, and 19.3 kilometres from Sarasota Bradenton International Airport.
This property provides accommodation for up to 11 guests, featuring 112 square metres of floor area, two bathrooms, a well-equipped kitchen, air conditioning, a swimming pool, a balcony with sea views, and on-site parking, with complimentary Wi-Fi and access to a fitness centre and tennis court.

Frequently asked questions about villa rentals in Siesta Key, FL

  • What are the must-see attractions in and around Siesta Key, FL?

    Siesta Key is known for its beautiful beaches, so you'll definitely want to spend some time on Siesta Key Beach, which is consistently ranked as one of the best beaches in the USA. You can also visit the Siesta Key Drum Circle, a popular gathering spot for musicians and locals, or take a stroll along the Siesta Key Village, which is home to shops, restaurants, and bars.
  • What are the best villa rentals in Siesta Key, FL?

    Among the villa rentals in Siesta Key, FL, Crescent Beach 1011 #1, Across The Street From #1 Beach and Siesta Key Beachside Villas are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Siesta Key, FL?

    You'll see plenty of birds, including pelicans, gulls, and herons, plus dolphins and manatees in the waters off the coast. Keep an eye out for the occasional alligator in the mangrove swamps and the rare sighting of a sea turtle nesting on the beach.
  • What are the best villa rentals with a pool in Siesta Key, FL?

    Crescent Beach 1011 #1, Siesta Key Beachside Villas and Siesta Key Beach Resort And Suites are the best villa rentals with a pool in Siesta Key, FL.

  • What is the best time to visit Siesta Key, FL?

    The best time to visit Siesta Key is during the shoulder seasons, from April to May and September to October, when the weather is still warm but the crowds are smaller. You can also enjoy a quieter experience during the winter months, but it can get a bit chilly.
  • What are the best villa rentals with a jacuzzi in Siesta Key, FL?

  • When is it easiest to book a villa rental in Siesta Key, FL?

    You'll find the best deals on villa rentals in Siesta Key during the off-season, from November to March. If you're looking to book during peak season, it's best to book as far in advance as possible, especially if you want a specific property.
  • What are the best villa rentals for families and kids in Siesta Key, FL?

    The best villa rentals for families and kids in Siesta Key, FL are Crescent Beach 1011 #1, Across The Street From #1 Beach and Siesta Key Beachside Villas.

  • What are the top hiking trails near Siesta Key, FL?

    There aren't many hiking trails in Siesta Key itself, as it's mostly a beach community. However, there are some great trails nearby at the Myakka River State Park, just a short drive away. There you can hike through the beautiful Florida wilderness and see a variety of wildlife.
  • What are the best pet friendly villa rentals in Siesta Key, FL?

  • What are the advantages of renting a house or a villa in Siesta Key, FL

    Renting a villa offers more space and privacy than a hotel room, and you can enjoy the comforts of home, such as a full kitchen and laundry facilities. You'll also have access to amenities like a private pool and a barbecue grill, which can make your vacation even more enjoyable.
  • What are the best villa rentals with parking in Siesta Key, FL?

    Crescent Beach 1011 #1, Across The Street From #1 Beach and Siesta Key Beachside Villas are the best villa rentals with parking in Siesta Key, FL.

  • Are there popular destinations near Siesta Key, FL?

    Yes, there are plenty of popular destinations near Siesta Key, such as Sarasota, which is home to the Ringling Museum and the Van Wezel Performing Arts Hall. You can also visit the nearby beaches of Lido Key and Longboat Key, or take a day trip to the Everglades.

Popular destinations

Best Siesta Key, FL villas and holiday homes with air conditioning

Tiny House Siesta - Siesta Key, FL
8.5 1199 reviews

Tiny House Siesta

house, Gulf Gate Estates
Tiny House Siesta is located in Sarasota, Florida, just a short walk from the famous Siesta Key Beach and close to the vibrant Gulf Gate Estates area. The accommodation has received very good ratings for its cleanliness, location, and overall experience.
The mobile home offers a unique and cosy living space with some units featuring two levels. Guests can enjoy a range of amenities including a kitchen, air conditioning, a terrace, a garden, and free Wi-Fi.
Siesta Key Beach - Tropea 665 #3 - Siesta Key, FL
9.4 269 reviews

Siesta Key Beach - Tropea 665 #3

house, Siesta Key
This Siesta Key holiday home is just a short walk from Crescent Beach and a 10-minute drive from The John and Mable Ringling Museum of Art, offering a peaceful escape from the bustling tourist areas. Guests consistently rate the property excellent for its location, cleanliness, and overall experience.
The single-bedroom property features a separate bedroom for privacy and a fully equipped kitchen with a dishwasher and oven. Guests can enjoy air conditioning, a TV with cable channels, and access to a spa, restaurant, and parking.
The Beach Club At Siesta #200c - Siesta Key, FL
No reviews

The Beach Club At Siesta #200c

house, Siesta Key
This holiday home is in the Point O'Rocks district of Siesta Key, a 2-minute walk from Crescent Beach and 17.7 kilometres from the Ringling Museum of Art and Sarasota Bradenton International Airport.
This 71 square metre holiday home accommodates up to 11 guests across 2 bedrooms and features a kitchen, air conditioning, a swimming pool, a hot tub, a fitness centre, tennis court, garden, and private parking, with a patio and laundry facilities also provided.
The Beach Club At Siesta #102b - Siesta Key, FL
8.0 1 review

The Beach Club At Siesta #102b

house, Siesta Key
This holiday home in Point O'Rocks is just steps from Crescent Beach, 17.7 kilometres from the John and Mable Ringling Museum of Art, and 17.7 kilometres from Sarasota Bradenton International Airport.
This 49-square-metre bungalow accommodates up to seven guests and offers a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, garden, fitness centre, tennis court, and private parking.

Best Siesta Key, FL villas and holiday homes with jacuzzi

6415 Midnight Pass #Ph8 - Siesta Key, FL
No reviews

6415 Midnight Pass #Ph8

house, Siesta Key
6415 Midnight Pass #PH8, a Siesta Key holiday home, is situated 1.1km from Crescent Beach, 2.6km from Turtle Beach, and 2.9km from Siesta Key Beach, offering convenient access to these popular destinations and being 18km from The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 116 square metre property boasts two bedrooms, two bathrooms, sleeping up to eleven guests, and features a private balcony, swimming pool, jacuzzi, sauna, spa, fitness centre, tennis court, and parking, alongside a fully equipped kitchen and free Wi-Fi.
Cozy Cottage Near Siesta Key Village! - Siesta Key, FL
9.0 2 reviews

Cozy Cottage Near Siesta Key Village!

cottage, Siesta Key
This cottage in Siesta Key is located just 150 metres from Siesta Beach and a short walk from Siesta Key Village.
This 51 square metre holiday home sleeps four guests and features two bedrooms, one bathroom, a private kitchen and living room, with access to a shared swimming pool and hot tub, plus complimentary bicycle rentals and beach equipment.
Jellyfish Unit, Walk To Beach & Siesta Key Village, Pet-friendly - Siesta Key, FL
8.5 2 reviews

Jellyfish Unit, Walk To Beach & Siesta Key Village, Pet-friendly

house, Siesta Key
This Siesta Key holiday home is a 0.6km stroll from Siesta Key Beach and under 1.6km from Crescent Beach, offering easy access to both stunning stretches of sand.
The 93 square metre property boasts two bedrooms, one bathroom, sleeps up to 19 guests, and includes a private pool, jacuzzi, and fully equipped kitchen; free Wi-Fi and parking are also provided.
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