Villas and Holiday homes in Siesta Key, FL

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Siesta Key, FL holiday homes
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2200 Villa rentals in Siesta Key, FL

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

Among the 2200 accommodations in Siesta Key, FL, here are the 4 best villas and holiday homes with a pool

Lakefront Siesta Key Condo With Private Beach Access - Siesta Key, FL
9.3 3 reviews

Lakefront Siesta Key Condo With Private Beach Access

house, Siesta Key
This Siesta Key condo, near Crescent Beach, is approximately 11 kilometres from Sarasota Opera House and 18 kilometres from The Ringling Museum.
The 102-square-metre property boasts two bedrooms, two bathrooms, sleeps nine guests, and includes a private pool, sauna, fitness centre, tennis court, and free Wi-Fi; enjoy easy access to Crescent Beach and the property's lakefront location with private beach access.
The Beach Club At Siesta #106d - Siesta Key, FL
10 1 review

The Beach Club At Siesta #106d

house, Siesta Key
This holiday cottage in Point O'Rocks, Siesta Key, offers direct access to Crescent Beach, situated 17.7 kilometres from the John and Mable Ringling Museum of Art and 19.3 kilometres from Sarasota International Convention Centre.
This 75 square metre villa accommodates up to 11 guests with 2 bathrooms, featuring a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, jacuzzi, garden, fitness centre, tennis court, and private parking, with cycling opportunities nearby.
Palm Shade Cottage | Charming 1-bedroom In Sk, Access To Pool, Walk To Beach! - Siesta Key, FL
9.6 10 reviews

Palm Shade Cottage | Charming 1-bedroom In Sk, Access To Pool, Walk To Beach!

cottage, Siesta Key
Palm Shade Cottage, situated in Siesta Key, Florida, is located just 0.16 km from Siesta Key Beach and a short walk from Siesta Key Village.
This one-bedroom holiday home, boasting 62 square metres of floor space, features a queen-sized bed, a Murphy bed, two bathrooms, a fully equipped kitchen, a private patio, and access to a shared heated pool (November 15th–April 15th), accommodating up to four guests.
186 M² House ∙ 4 Bedrooms ∙ 12 Guests - Siesta Key, FL
10 34 reviews

186 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Siesta Key
Casa Antilles, a Siesta Key duplex, is situated on the southern end of the island, a 0.3km stroll from Crescent Beach and Point of Rocks, and under 1.6km from Crescent Village, offering easy access to both beach and local amenities.
This 185 square metre, four-bedroom, three-bathroom property sleeps up to twelve guests, boasting a private heated pool, expansive outdoor entertainment area with cabana, fully equipped kitchen, and convenient amenities including a private lift, gas grill, ping pong table, and beach supplies.

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

[Beach Elements] Pool View Withprivate Beach Access - Siesta Key, FL
9.6 37 reviews

[Beach Elements] Pool View Withprivate Beach Access

house, Siesta Key
This Siesta Key apartment is conveniently located a short walk from Siesta Key Beach and St Boniface Episcopal Church Labyrinth, with Crescent Beach approximately 3.2 kilometres away.
The self-catering flat sleeps four, boasts a fully equipped kitchen, patio, swimming pool, parking, and is within easy reach of local amenities; a washing machine and sofa bed are additional features.
Villa Castile - 5204 - Siesta Key, FL
10 3 reviews

Villa Castile - 5204

house, Siesta Key
Villa Castile - 5204 is situated in Siesta Key, Florida, an 8-minute walk (approximately 1.3km) from Siesta Key Beach and 2km from Crescent Beach, offering easy access to local attractions.
This three-bedroom, three-bathroom property boasts 133 square metres of living space, accommodating up to 19 guests, and includes a private pool, fully equipped kitchen, free Wi-Fi, and free private parking.
Beautiful Property On Siesta Key - Siesta Key, FL
8.1 61 reviews

Beautiful Property On Siesta Key

house, Siesta Key
This charming two-bedroom villa is located on Siesta Key, a mere 0.8km from Crescent Beach and 1.6km from Siesta Key Beach. The property has received excellent ratings for its location, cleanliness, and overall experience.
The villa spans 100 square metres and comfortably accommodates up to four guests. Enjoy a private pool, patio, garden, and a fully equipped kitchen, along with access to a private beach area, fishing opportunities, and a barbecue.
Casita East - Siesta Key, FL
No reviews

Casita East

house, Siesta Key
This Casita East property is located in Point O'Rocks, Siesta Key, a 3-minute walk from Crescent Beach and approximately 17.7 kilometres from the John and Mable Ringling Museum of Art.
This 63 square metre bungalow offers accommodation for up to 7 guests, featuring 1 bedroom, 1 bathroom, air conditioning, a kitchen with a fridge, microwave, and dishwasher, a terrace, swimming pool access, and complimentary private parking.

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

Charming Beachside Retreat - Aloha Kai #18 - Roelens - Siesta Key, FL
10 1 review

Charming Beachside Retreat - Aloha Kai #18 - Roelens

house, Siesta Key
This detached house is situated in Siesta Key, mere steps from Crescent Beach, 12.7 kilometres from downtown Sarasota's Marina Jack and Opera House, and 17.7 kilometres from the John and Mable Ringling Museum of Art.
This property offers 700 square metres of living space for up to three guests, featuring one bedroom and one bathroom, with amenities including air conditioning, WiFi, a swimming pool, spa, and on-site parking, plus access to a water park.
Heated Pool, Dock, Kayaks, 1-mile To Turtle Beach - Siesta Key, FL
9.8 43 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.
Canal 309 - Right In Siesta Key Village! - Siesta Key, FL
9.3 73 reviews

Canal 309 - Right In Siesta Key Village!

house, Siesta Key
Canal 309, a Siesta Key Village property, is situated a short walk from Siesta Key Beach and a short drive (approximately 0.6 km) from Crescent Beach, the Ringling Museum, and Sarasota Opera House.
This two-bedroom, two-bathroom holiday home boasts 93 square metres of living space, a private pool, free Wi-Fi, and parking; it also offers barbecue facilities, and nearby bicycle rentals for exploring the island.
Siesta Key Beach | Remote Worker Friendly | Bikes - Siesta Key, FL
9.3 3 reviews

Siesta Key Beach | Remote Worker Friendly | Bikes

cabin, Siesta Key
This studio apartment is situated in Siesta Key, a brief walk from Siesta Key Beach, consistently rated number one.
This 14 square metre tiny house offers accommodation for two guests, featuring a designated remote work space that converts from a queen bed, a compact kitchen with a retro mini refrigerator and a versatile 6-in-1 oven, and an all-in-one washer and dryer.

Best Siesta Key, FL villas and holiday homes with jacuzzi

The Beach Club At Siesta #108a - Siesta Key, FL
No reviews

The Beach Club At Siesta #108a

house, Siesta Key
This detached house in Point O'Rocks, Siesta Key, offers prime accommodation just 100 metres from Crescent Beach, 17.7 kilometres from the John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This property boasts a 74 square metre floor area, accommodates up to 11 guests across 2 bedrooms and 2 bathrooms, and features a fully equipped kitchen, air conditioning, a swimming pool, hot tub, fitness centre, tennis court, and private parking, with disabled guest facilities available.
Walk To Siesta Key Beach And Village W Pool - Siesta Key, FL
No reviews

Walk To Siesta Key Beach And Village W Pool

house, Siesta Key
This holiday cottage is located in Siesta Key, a short walk from Siesta Key Beach and Village, and 16 kilometres from the John and Mable Ringling Museum of Art.
This one-bedroom, one-bathroom property accommodates up to four guests and features a kitchen with a fridge and microwave, air conditioning, a swimming pool, jacuzzi, garden, fitness centre, parking, and complimentary WiFi.
Siesta Key Canal: Pool & Boat - Siesta Key, FL
No reviews

Siesta Key Canal: Pool & Boat

house, Siesta Key
This luxurious four-bedroom villa is located on the Grand Canal in Siesta Key, a short walk from Siesta Key Village and the beach.
This opulent property offers accommodation for fourteen guests, featuring a private swimming pool, jacuzzi, garden, and parking, with a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher.
Luxe Siesta Key Home Pool Hot Tub Near Beach - Siesta Key, FL
9.0 1 review

Luxe Siesta Key Home Pool Hot Tub Near Beach

house, Siesta Key
This Siesta Key holiday home is situated a 1.6km stroll from Siesta Key Beach and 2.7km from Crescent Beach, offering easy access to Sarasota Bradenton International Airport (within 18km).
The 159 square metre property boasts three bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, hot tub, fully equipped kitchen, and electric vehicle charging point.
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