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

Canal 313 - Right In Siesta Key Village! - Siesta Key, FL
9.2 192 reviews

Canal 313 - Right In Siesta Key Village!

house, Siesta Key
Canal 313, a renovated holiday home in Siesta Key Village, is situated a short distance from Siesta Key Beach and 2.1 kilometres from Crescent Beach, offering easy access to local amenities and the Ringling Museum of Art (within 16 kilometres).
This 93-square-metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, a private swimming pool, tennis court, free Wi-Fi, and parking; ideal for families or small groups seeking a relaxing Siesta Key getaway.
Private Beach Retreat On Siesta Key! Bright Villa - Siesta Key, FL
9.6 5 reviews

Private Beach Retreat On Siesta Key! Bright Villa

house, Siesta Key
This beachfront villa in Siesta Key offers direct access to the sand and sea, situated just a 3-minute walk from Crescent Beach and 12.2 kilometres from Marina Jack and the Sarasota Opera.
This spacious two-bedroom flat, accommodating up to 11 guests, features two bathrooms, a fully equipped kitchen, complimentary Wi-Fi, a private patio and terrace with sea views, and access to an outdoor swimming pool.
Heated Pool, Dock, Kayaks, 1-mile To Turtle Beach - Siesta Key, FL
10 49 reviews

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

bungalow, Siesta Key
This Siesta Key bungalow in Vamo, Florida, offers convenient access to Heron Lagoon and its dock.
The self-catering property sleeps three guests in one bedroom and one bathroom, boasting a private veranda, a fully equipped kitchen, free Wi-Fi, and access to a shared heated pool and complimentary beach gear for Heron Lagoon.
70 M² House ∙ 1 Bedroom ∙ 4 Guests - Siesta Key, FL
No reviews

70 M² House ∙ 1 Bedroom ∙ 4 Guests

house, Siesta Key
Aloha Kai #51, a 70 square meter holiday cottage, offers direct access to Crescent Beach, ranked the USA's top beach, and is a short stroll to local eateries and bars, with the Siesta Key trolley conveniently nearby.
This family-friendly accommodation sleeps four guests and boasts the largest pool on Siesta Key, a sunroom, complimentary beach toys, and access to community amenities including shuffleboard and ping pong.

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

House ∙ 1 Bedroom ∙ 2 Guests - Siesta Key, FL
10 3 reviews

House ∙ 1 Bedroom ∙ 2 Guests

house, Siesta Key
Aloha Kai #18, a beach studio in the Aloha Kai resort on Crescent Beach, Siesta Key, offers direct access to this top-rated US beach and is a short walk from local restaurants and bars.
This self-catering apartment, sleeping two guests, features a king-size bed, Smart TV, private screened porch, access to a large resort pool and spa, plus community amenities including shuffleboard and complimentary beach toys.
Gorgeous 3 Br Home Minutes From Siesta Key - Edgewater Bungalow - Siesta Key, FL
9.0 6 reviews

Gorgeous 3 Br Home Minutes From Siesta Key - Edgewater Bungalow

house, Gulf Gate Estates
This 2-bedroom detached house in Gulf Gate Estates, Sarasota, is situated approximately 9.8 kilometres from Marina Jack Restaurant and Marina and 9.9 kilometres from Sarasota Opera, with Siesta Key just minutes away.
This detached house offers 164 square metres of living space, accommodating up to 11 guests with a fully equipped kitchen, air conditioning, complimentary Wi-Fi, on-site parking, and a children's playground.
Canal Upper-gorgeous 3 Bed 3 Bath Near Sk Village - Siesta Key, FL
9.5 219 reviews

Canal Upper-gorgeous 3 Bed 3 Bath Near Sk Village

house, Siesta Key
This Siesta Key house is just 0.8 kilometres from the famous Siesta Key Beach and 2.1 kilometres from Crescent Beach, offering easy access to the beautiful white sand and turquoise waters. It has excellent user, location and cleanliness ratings.
The house has three bedrooms and three bathrooms, comfortably accommodating a family or group of friends. It comes with a private pool, a hot tub, a fully equipped kitchen, free Wi-Fi, cable TV, and parking.
Heated Pool, Dock, Kayaks, 1-mile To Turtle Beach - Siesta Key, FL
9.8 67 reviews

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

bungalow, Siesta Key
This Siesta Key bungalow, part of The Siesta Key Bungalows, is situated in Vamo, Florida, offering direct access to Heron Lagoon and proximity to Siesta Key Beach (exact distance unspecified).
The self-catering unit sleeps three, boasting a king-size bed, a roll-away bed, a private veranda overlooking Heron Lagoon with a private dock, free kayak use, and access to a shared heated pool, BBQ grills, and complimentary beach gear; free laundry facilities and contactless check-in are also available.

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

Crescent Royale Condominiums108 - Siesta Key, FL
9.0 1 review

Crescent Royale Condominiums108

house, Siesta Key
Crescent Royale 108 is a self-catering property situated in Siesta Key, Florida, a 0.64km stroll from Siesta Key Beach and 17.7km from the John and Mable Ringling Museum of Art.
This 83 square metre house features one bedroom, one bathroom, sleeps seven guests, and boasts a private pool, free Wi-Fi, on-site parking, a balcony with sea views, and a fully equipped kitchen.
Casita West - Siesta Key, FL
No reviews

Casita West

house, Siesta Key
Casita West is situated in Point O'Rocks, a 3-minute walk from Crescent Beach, and approximately 17.7 to 19.3 kilometres from the John and Mable Ringling Museum of Art and Sarasota International Convention Centre.
This 63 square metre holiday home offers accommodation for up to 7 guests with 1 bedroom and 1 bathroom, featuring a fully equipped kitchen with a dishwasher, air conditioning, a swimming pool, a terrace, and on-site water park access, with complimentary private parking and WiFi available.
Beach Access - Tennis - Two Pools - Fishing Dock - Siesta Key, FL
10 4 reviews

Beach Access - Tennis - Two Pools - Fishing Dock

house, Siesta Key
This Siesta Key villa is situated 11 kilometres from The John and Mable Ringling Museum of Art and 12 kilometres from Sarasota International Convention Centre, with direct beach access to Crescent Beach just 600 metres away.
This air-conditioned holiday home offers 105 square metres of living space with two bedrooms accommodating up to seven guests, featuring a swimming pool, sauna, tennis court, and complimentary Wi-Fi.
Peaceful Lakefront Condo On Siesta Key - Private Beach Access, 2 Pools, Tennis And Pickleball Courts - Siesta Key, FL
10 1 review

Peaceful Lakefront Condo On Siesta Key - Private Beach Access, 2 Pools, Tennis And Pickleball Courts

house, Siesta Key
This Siesta Key lakefront apartment is a 7-minute walk from Crescent Beach and 18km from the John and Mable Ringling Museum of Art, offering private beach access.
The 89-square-metre property boasts two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, air conditioning, a balcony, a swimming pool, on-site parking, a sauna, and access to tennis courts.

Best Siesta Key, FL villas and holiday homes with jacuzzi

Blue Lagoon - Siesta Key, FL
No reviews

Blue Lagoon

house, Siesta Key
This Siesta Key holiday home, Blue Lagoon, is a six-minute walk from Crescent Beach and less than 1.6km from Siesta Key Beach, famed for its quartz sand.
The 334 square metre property boasts one bedroom, five bathrooms, sleeps eighteen guests, and includes a private terrace, swimming pool, fully equipped kitchen, and free Wi-Fi.
Hyatt Residences On Siesta Key Beach - A Premier Hotel Experience! - Siesta Key, FL
9.0 4 reviews

Hyatt Residences On Siesta Key Beach - A Premier Hotel Experience!

house, Siesta Key
This holiday home offers direct access to Crescent Beach in Siesta Key, situated 17 kilometres from the John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 163 square metre property sleeps up to 11 guests across three bedrooms, featuring a private balcony, hot tub, spa, fitness centre, sauna, and air conditioning, with Wi-Fi and parking provided.
Walk To Siesta Key Beach And Village - Siesta Key, FL
No reviews

Walk To Siesta Key Beach And Village

house, Siesta Key
This holiday home is situated in Siesta Key, a 5-minute walk from Siesta Key Beach and Siesta Key Village, with the Ringling Museum complex 16 kilometres away.
This one-bedroom bungalow accommodates up to five guests and offers a kitchen with a fridge and microwave, air conditioning, a swimming pool, hot tub, garden, on-site restaurant, fitness centre, and parking, with complimentary WiFi available.
High Tide - Siesta Key, FL
No reviews

High Tide

house, Siesta Key
High Tide, a Siesta Key holiday home, is situated a 0.6km stroll from Siesta Key Beach, 2.3km from Crescent Beach, 16km from the Ringling Museum of Art, and 10km from the Sarasota Opera House.
This six-bedroom, six-bathroom property boasts 337 square metres of living space, comfortably accommodating up to 35 guests and offering a private pool, terrace, free Wi-Fi, and parking; laundry facilities are also available.
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