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

100 Percent Private - Pool, Oceanviews, Village, Beaches! - Siesta Key, FL
No reviews

100 Percent Private - Pool, Oceanviews, Village, Beaches!

house, Siesta Key
This Siesta Key holiday home is a two-minute walk from Siesta Key Beach, 2.4 kilometres from Crescent Beach, and 18 kilometres from Sarasota Bradenton International Airport.
This eight-bedroom property boasts 557 square metres of living space, including two living rooms, six bathrooms, a private pool, and a spa, comfortably accommodating up to 51 guests and offering free Wi-Fi and parking.
Heated Pool And Beach Access - Charming Coastal Haven - Siesta Key, FL
No reviews

Heated Pool And Beach Access - Charming Coastal Haven

house, Siesta Key
This Siesta Beach House, Cottage B, is located in Siesta Key, a mere 400 metres from Siesta Key Public Beach and a short walk to a heated community pool.
This family-friendly cottage accommodates up to eight guests with three bedrooms and two bathrooms, offering a fully equipped kitchen, air conditioning, a swimming pool, spa, and parking.
Walk To Beach: Condo W/ Pool & Patio In Sarasota! - Siesta Key, FL
9.2 39 reviews

Walk To Beach: Condo W/ Pool & Patio In Sarasota!

house, Siesta Key
This apartment is located in Sarasota, just a short 6-minute walk from Crescent Beach and a 10-minute drive from Siesta Key, offering easy access to the beautiful beaches and vibrant nightlife of the area. The property has received excellent user ratings for cleanliness and location, indicating a comfortable and well-maintained stay.
The apartment has two bedrooms, a living room, and a fully equipped kitchen, covering 84 square metres of space. Guests can enjoy a private patio, a refreshing swimming pool, and a spa, along with free Wi-Fi and parking.
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.

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

16 Guest Pool House Walk To The Beach And Village - Siesta Key, FL
9.7 88 reviews

16 Guest Pool House Walk To The Beach And Village

apartment, Siesta Key
This Siesta Key house is situated just under 3 kilometres from Siesta Key Beach, and within 5 kilometres of both Shell Beach and Crescent Beach. It is located in Siesta Key Village, a quiet and relaxing area, offering a peaceful retreat from the hustle and bustle of more crowded areas. Guests have rated this property excellent for location, cleanliness and overall experience.
The property is a 6-bedroom house that provides ample space for large families or groups of friends. It offers modern amenities, including free Wi-Fi, a fully equipped kitchen, a private pool, a fenced private yard, and barbecue grills.
Beach Rd, 300ft To Beach Access & 500ft To Siesta Key Village, 2bdr - Siesta Key, FL
9.2 10 reviews

Beach Rd, 300ft To Beach Access & 500ft To Siesta Key Village, 2bdr

chalet, Siesta Key
This Siesta Key Village holiday home is less than 1.6km from Siesta Key Beach and Farmers Market, and within 3.2km of Siesta Key Beach Playground and St. Boniface Episcopal Church Labyrinth.
The 74 square metre property sleeps seven guests across three bedrooms and two bathrooms, offering a kitchen with fridge, microwave, and dishwasher, air conditioning, a terrace, garden, parking, and Wi-Fi.
Clean, Modern And Newly Renovated Condo On Us #1 Private Siesta Key Beach - Siesta Key, FL
9.8 256 reviews

Clean, Modern And Newly Renovated Condo On Us #1 Private Siesta Key Beach

apartment, Siesta Key
This Siesta Key apartment is situated less than 2km from Siesta Key Beach and Crescent Beach, also within 1.6km of Siesta Key Marina and St Boniface Episcopal Church Labyrinth.
Offering a one-bedroom, one-bathroom flat with a private pool, free WiFi, fully equipped kitchen, and access to a shared garden and barbecue facilities, this pet-friendly property sleeps up to two guests and includes a patio and Smart TV.
Minorga On The Gulf - Siesta Key, FL
9.5 37 reviews

Minorga On The Gulf

house, Siesta Key
Minorga on the Gulf, a Siesta Key holiday home, is a 7-minute walk from Siesta Key Beach and within 9.6-16 kilometers of Sarasota attractions including the Ringling Museum of Art and Sarasota Opera House.
This self-catering property boasts a fully equipped kitchen, swimming pool, free Wi-Fi, and private parking; it is suitable for adults aged 25 and over.

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

The Upper Deck - Siesta Key, FL
10 20 reviews

The Upper Deck

house, Siesta Key
The Upper Deck is a six-bedroom house in Siesta Key, Florida, a three-minute walk from Siesta Key Beach and 1.8 kilometres from Crescent Beach, with the John and Mable Ringling Museum of Art ten miles away.
This luxury property boasts a private hot tub, elevator, and sun terrace, offering ample space for large groups or families with a fully equipped kitchen, outdoor dining area and on-site mini-golf.
Siesta Royale 47 - Siesta Key, FL
No reviews

Siesta Royale 47

house, Siesta Key
This Siesta Key villa, located in the Siesta Royale district, is a mere 2-minute walk from Crescent Beach and within 320 metres of Parasail Siesta.
This 58 square metre accommodation offers one bedroom and one bathroom, comfortably sleeping up to seven guests with a fully equipped kitchen, air conditioning, and free on-site parking.
Siesta Key Village, Heated Pool, Beach Access 4 Min Walk, 1bdr - Siesta Key, FL
9.3 7 reviews

Siesta Key Village, Heated Pool, Beach Access 4 Min Walk, 1bdr

house, Siesta Key
This Siesta Key Village apartment is an 8-minute walk from Siesta Key Beach, 2.1km from Crescent Beach, and 16km from The John and Mable Ringling Museum of Art.
The 56-square-metre property boasts one bedroom, one bathroom, sleeps seven guests, and includes a private patio with pool views, a heated pool, free Wi-Fi, and free private parking, plus BBQ facilities and laundry service.
Casa Mar - 29 Standard Plus - Siesta Key, FL
No reviews

Casa Mar - 29 Standard Plus

house, Siesta Key
This detached holiday home is located in Siesta Key, within the 34242 postal code, offering convenient access to local attractions.
This property accommodates up to three guests in one bedroom and features a fully equipped kitchen, air conditioning, free WiFi, private parking, and barbecue facilities for outdoor enjoyment.

Best Siesta Key, FL villas and holiday homes with jacuzzi

The Beach Club At Siesta #106b - Siesta Key, FL
No reviews

The Beach Club At Siesta #106b

house, Siesta Key
This holiday cottage is situated in Point O'Rocks, mere steps from Crescent Beach, and 17.7 kilometres from the John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 75 square metre, two-bedroom holiday home accommodates up to 11 guests and features a fully equipped kitchen, private patio, access to a shared heated swimming pool, hot tub, fitness room, and complimentary WiFi and parking.
6415 Midnight Pass #210 - Siesta Key, FL
No reviews

6415 Midnight Pass #210

house, Siesta Key
This Siesta Key holiday home, 6415 Midnight Pass #210, is a 7-minute walk from Crescent Beach, 2.6 km from Turtle Beach, and 2.9 km from Siesta Key Beach, offering convenient access to local attractions including the John and Mable Ringling Museum of Art (18 km away).
The 116-square-metre property boasts two bedrooms, two bathrooms, and sleeps up to 11 guests, featuring a private pool, jacuzzi, sauna, and fitness centre, alongside free Wi-Fi and a fully equipped kitchen.
211 M² House ∙ 5 Bedrooms ∙ 10 Guests - Siesta Key, FL
10 21 reviews

211 M² House ∙ 5 Bedrooms ∙ 10 Guests

house, Sarasota
This luxurious Sarasota holiday home is situated on Siesta Key, a short drive from Siesta Key Beach and within walking distance of restaurants and a Publix supermarket, offering easy access to Sarasota city centre.
The 210 square metre property boasts four king-size bedrooms sleeping up to ten guests, a private heated saltwater pool and spa, a fully equipped gourmet kitchen including a wine cooler and air fryer, and a ten-seat tiki bar with a 60" TV – perfect for family holidays.
Heated Pool And Beach Access Just Steps Away - Stunning Oasis - Siesta Key, FL
No reviews

Heated Pool And Beach Access Just Steps Away - Stunning Oasis

house, Siesta Key
This spacious two-storey townhouse offers an exceptional location in Siesta Key, just 10 steps from Siesta Village and a 5-minute walk to the beach, with the SRQ Airport less than 30 kilometres away.
Accommodating up to 10 guests, this holiday home features three bedrooms, two bathrooms (one en-suite with a jet tub and balcony), an open-plan living area, and access to a shared heated swimming pool, BBQ, and complimentary high-speed internet.
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