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

Renovated Siesta Key Villa+private Beach+3 Pools - Siesta Key, FL
10 12 reviews

Renovated Siesta Key Villa+private Beach+3 Pools

house, Siesta Key
This villa is situated within a private, gated beachfront complex on Siesta Key, offering direct access to the beach just a 3-minute walk away, and a convenient 5-minute free trolley ride to Siesta Key Village.
This property boasts a heated beachfront swimming pool, two additional heated pools, a private dining patio, and modern furnishings, accommodating up to six guests with a kitchen featuring a fridge, freezer, microwave, and dishwasher, plus complimentary internet and air conditioning.
Siesta Key Village, Pool, Beach Access 4-min Walk - Siesta Key, FL
9.9 59 reviews

Siesta Key Village, Pool, Beach Access 4-min Walk

house, Siesta Key
This Siesta Key Village townhouse is situated a short walk (less than 0.8 km) from Siesta Beach and the shops and restaurants of Siesta Key Village.
The three-bedroom property sleeps up to ten guests, boasting a private heated pool, jacuzzi, and fully equipped kitchen; beach essentials and optional services like mid-stay cleaning are also available.
Casa Blanca - Villa D16 - Siesta Key, FL
No reviews

Casa Blanca - Villa D16

house, Siesta Key
This newly renovated two-bedroom, one-bathroom villa offers unparalleled proximity to Siesta Key Beach, situated just a few steps from the city centre and a short 3.5 kilometre drive to the shops at St. Armands Circle.
This accommodation sleeps four guests and features a fully equipped kitchen, air conditioning, a swimming pool, and outdoor shower, with the master bedroom including a queen-size bed and a 50-inch smart TV.
Lulu's Key House Green 1/1 Upstairs - Siesta Key, FL
9.0 5 reviews

Lulu's Key House Green 1/1 Upstairs

house, Siesta Key
LuLu's Key House Green 1/1 Upstairs is a self-catering property situated in Siesta Key, Florida, a six-minute walk from Siesta Key Beach and within 16km of Sarasota's attractions including the Ringling Museum and St. Armands Circle.
This one-bedroom, one-bathroom apartment offers 59 square metres of space, sleeping up to seven guests and boasting a swimming pool, free Wi-Fi, and private parking; it also benefits from a fully equipped kitchen and air conditioning.

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

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.
Beach Getaway! - Aloha Kai #42 - Roelens - Siesta Key, FL
9.7 3 reviews

Beach Getaway! - Aloha Kai #42 - Roelens

house, Siesta Key
This holiday home in Sarasota is located just a few steps from Crescent Beach and 17.7 kilometres from the John and Mable Ringling Museum of Art.
This property boasts 780 square metres of floor area, accommodates up to 7 guests with 1 bedroom and 1 bathroom, and offers a private entrance, a fully equipped kitchen, an outdoor swimming pool, a spa, a water park, a children's playground, and complimentary on-site parking and Wi-Fi.
100 Percent Private, Tiki-bar, 250steps To Beach And Village! - Siesta Key, FL
No reviews

100 Percent Private, Tiki-bar, 250steps To Beach And Village!

house, Siesta Key
This Siesta Key holiday home is a seven-minute walk from Siesta Key Beach, 1.9 kilometres from Crescent Beach, and within 10-18 kilometres of various Sarasota attractions.
This six-bedroom property boasts a 2787 square metre floor area, four bathrooms, a private Tiki bar, and can comfortably accommodate 43 guests, offering easy beach access and free Wi-Fi.
Beach Rd, 300ft To Beach Access & 500ft To Village - Siesta Key, FL
9.9 75 reviews

Beach Rd, 300ft To Beach Access & 500ft To Village

chalet, Siesta Key
This Siesta Key studio apartment is situated a mere 0.16km from Siesta Key Beach and under 0.8km from Siesta Village, offering easy access to restaurants and shops.
The self-catering unit features a queen-size bed, kitchenette with island, private balcony with partial ocean views, and complimentary beach essentials; it sleeps two guests and offers additional services including mid-stay cleaning and golf cart rentals.

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

House ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
10 1 review

House ∙ 2 Bedrooms ∙ 6 Guests

house, Siesta Key
This Aloha Kai #17 villa offers direct access to Crescent Beach, recognised as the USA's top beach, and is conveniently located within a 1-kilometre walk of restaurants and entertainment, accessible via the Siesta Key trolley.
This family-friendly property accommodates up to six guests in two bedrooms and one bathroom, featuring a large swimming pool, spa, air conditioning, Wi-Fi, a fully equipped kitchen, and complimentary beach equipment, all within the secure, gated Aloha Kai resort.
6415 Midnight Pass #202 - Siesta Key, FL
No reviews

6415 Midnight Pass #202

house, Siesta Key
6415 Midnight Pass #202, a Siesta Key holiday home, is conveniently located a 1.1km walk from Crescent Beach, 2.6km from Turtle Beach, and 2.9km from Siesta Key Beach.
This 116 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private balcony, swimming pool, jacuzzi, sauna, spa, fitness centre, tennis court, and free Wi-Fi.
Walk To Siesta Key Beach, Heated Pool And Numerous Restaurants/bars/shops - Siesta Key, FL
No reviews

Walk To Siesta Key Beach, Heated Pool And Numerous Restaurants/bars/shops

house, Siesta Key
This villa is located in Siesta Key's South Village, a short 300-metre walk from Siesta Key Beach and close to local dining, entertainment, and shopping facilities.
This 65 square metre, two-bedroom, one-bathroom retreat accommodates up to four guests and features a fully equipped kitchen, a private fenced backyard with a barbecue grill and outdoor dining area, a heated community swimming pool, and provided beach essentials.
Villa 3 · Pool View.  Walk To Beach. Daily Rentals - Siesta Key, FL
9.8 397 reviews

Villa 3 · Pool View. Walk To Beach. Daily Rentals

apartment, Siesta Key
This apartment is located in Siesta Key, just a short walk from Point of Rocks and Crescent Beach, and about 2.4 kilometres from the main Siesta Key Beach, offering a peaceful retreat away from the hustle and bustle. It consistently receives excellent ratings for location, cleanliness, and overall experience.
The apartment is a one-bedroom, one-bathroom flat that comfortably accommodates two guests. It comes equipped with a fully fitted kitchen, a private patio, and access to a communal swimming pool, barbecue facilities, and free Wi-Fi.

Best Siesta Key, FL villas and holiday homes with jacuzzi

The Beach Club At Siesta #100d - Siesta Key, FL
9.3 3 reviews

The Beach Club At Siesta #100d

house, Siesta Key
This holiday home in Point O'Rocks, Siesta Key, offers direct access to Crescent Beach, situated a mere 17.7 kilometres from the John and Mable Ringling Museum of Art.
This 56 square metre property accommodates up to 7 guests with 1 bathroom, 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 free WiFi provided.
056 Tower East View - Siesta Key, FL
No reviews

056 Tower East View

house, Siesta Key
This fifth-floor apartment in the Grand Tower Building offers a prime location just 150 metres from Siesta Key's famous white quartz sand beaches and warm Gulf waters.
This property accommodates up to four guests with two Queen-size beds, featuring a well-equipped kitchen, a Jacuzzi, spa access, and entertainment provided by two flat-screen televisions.
Beach Rd, 300ft To Beach Access & 500ft To Village - Siesta Key, FL
10 49 reviews

Beach Rd, 300ft To Beach Access & 500ft To Village

chalet, Siesta Key
This charming beach house is situated just 100 metres from the world-renowned Siesta Key Beach, a short 5-minute walk from the lively Siesta Village. This prime location offers easy access to the area's best restaurants, shops, and entertainment options.
The chalet comfortably accommodates up to 7 guests and features 2 bedrooms and 2 bathrooms. It includes a well-equipped kitchen, a private porch, and a shared outdoor deck with lounge chairs, perfect for relaxing and enjoying BBQs. Guests also benefit from complimentary beach essentials, including towels, chairs, blankets, an umbrella, and a beach cart.
277 M² House ∙ 5 Bedrooms ∙ 14 Guests - Siesta Key, FL
10 2 reviews

277 M² House ∙ 5 Bedrooms ∙ 14 Guests

house, Siesta Key
This detached house, named Paradise Cove, is situated just 161 metres from Siesta Key Beach and 0.4 miles from Siesta Key Village.
This spacious 277 square metre residence accommodates up to 14 guests, featuring 5 bedrooms and 5 bathrooms, a private pool with a spa, a putting green, and entertainment options like ping pong and foosball, with canal views and paddle access.
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