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

Lulu's Key House Green 1/1 Upstairs - Siesta Key, FL
9.0 6 reviews
Siesta Key, FL
06/07 – 09/07
386 €/nighttotal: 1158 € (3 )

Lulu's Key House Green 1/1 Upstairs

1 2
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.
139 M² House ∙ 3 Bedrooms ∙ 10 Guests - Siesta Key, FL
9.7 14 reviews
Siesta Key, FL
30/07 – 01/08
1351 €/nighttotal: 2702 € (2 )

139 M² House ∙ 3 Bedrooms ∙ 10 Guests

3 7
house , Siesta Key
Casita Morning Star, a three-bedroom duplex in South Siesta Key, is a three-minute walk from Crescent Beach and Point of Rocks, and a short drive from Siesta Key Village and Siesta Key Beach.
This 139 square metre property sleeps up to ten guests, boasting three bathrooms, a private heated pool (heated 15 November–15 April), a fully equipped kitchen with gas grill, free Wi-Fi, four HDTVs, and provided beach essentials; one dog up to 25lbs is permitted (fee applies).
Casa Mar - 64 Premium - Siesta Key, FL
8.0 1 review
Siesta Key, FL
06/07 – 13/07
262 €/nighttotal: 1834 € (7 )

Casa Mar - 64 Premium

1 2
house , Siesta Key
Casa Mar - 64 Premium, situated in Sarasota, offers a one-bedroom property a short 0.5km stroll from Crescent Beach and under 1.5km from Siesta Key Beach.
This self-catering house sleeps seven, boasting a swimming pool, tennis court, and free Wi-Fi, alongside kitchen appliances including a fridge, microwave, and dishwasher, making it ideal for families or groups visiting Sarasota's attractions, such as the Ringling Museum (7-11 miles).
Crescent Royale Condominiums 209 - Siesta Key, FL
Siesta Key, FL
14/07 – 11/08
209 €/nighttotal: 5852 € (28 )

Crescent Royale Condominiums 209

1 3
house , Siesta Key
This Crescent Royale 209 apartment is situated in Siesta Key, a mere 4-minute walk from Siesta Key Beach, 17.7 kilometres from the John and Mable Ringling Museum of Art, and 19.3 kilometres from Sarasota Bradenton International Airport.
This one-bedroom apartment offers accommodation for up to five guests, featuring a well-equipped kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, a terrace, a fitness centre, tennis court, private parking, and a floor area of 83 square metres.

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

Full Beachfront Condo - Gulf View- Sunsets - Pool - Chairs - Siesta Key, FL
9.8 154 reviews
Siesta Key, FL
12/09 – 19/09
259 €/nighttotal: 1813 € (7 )

Full Beachfront Condo - Gulf View- Sunsets - Pool - Chairs

1 3
house , Siesta Key
This two-bedroom apartment is situated on Siesta Key, just 2.6 kilometres from Siesta Key Beach and 17.7 kilometres from the John and Mable Ringling Museum of Art.
The 93 square metre apartment offers a private beach area, a swimming pool, a garden, and free Wi-Fi and parking.
Island House Beach Resort V34 - Siesta Key, FL
9.2 9 reviews
Siesta Key, FL
04/07 – 08/07
609 €/nighttotal: 2436 € (4 )

Island House Beach Resort V34

2 4
house , Siesta Key
Island House Beach Resort V34 is a two-bedroom villa situated less than 1.6km from Crescent Beach and Siesta Key Beach, and 4.7km from Turtle Beach on Siesta Key.
This self-catering property sleeps four, offering a private patio, in-villa kitchen with refrigerator and microwave, laundry facilities, and access to an on-site barbecue area and games room.
Crescent Royale Condominiums 107 - Siesta Key, FL
Siesta Key, FL
30/07 – 09/08
280 €/nighttotal: 2800 € (10 )

Crescent Royale Condominiums 107

2 5
house , Siesta Key
Crescent Royale 107, a two-bedroom property in Siesta Key, Florida, is a four-minute walk from Siesta Key Beach and approximately 18km from Sarasota–Bradenton International Airport and various Sarasota attractions including the Ringling Museum of Art.
This 112 square metre self-catering apartment sleeps up to 11 guests and boasts a private balcony with sea views, a well-equipped kitchen, two bathrooms, on-site parking, Wi-Fi, pool access, and is close to Marina Jack Restaurant and Marina.
Canal 315 - Right In Siesta Key Village! - Siesta Key, FL
9.0 179 reviews
Siesta Key, FL
01/08 – 06/08
459 €/nighttotal: 2295 € (5 )

Canal 315 - Right In Siesta Key Village!

2 5
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.

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.

Destinations nearby

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

Canal Upper-gorgeous 3 Bed 3 Bath Near Sk Village - Siesta Key, FL
9.5 200 reviews
Siesta Key, FL
04/07 – 08/07
542 €/nighttotal: 2168 € (4 )

Canal Upper-gorgeous 3 Bed 3 Bath Near Sk Village

3 4
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.
Crescent Royale Condominiums 205 - Siesta Key, FL
Siesta Key, FL
18/07 – 25/07
253 €/nighttotal: 1771 € (7 )

Crescent Royale Condominiums 205

1 2
house , Siesta Key
This Crescent Royale 205 apartment is located in Siesta Key, a four-minute walk from Siesta Key Beach, 17.7 kilometres from the Ringling Museum of Art, and 19.3 kilometres from Sarasota Bradenton International Airport.
This one-bedroom apartment, with space for up to five guests, offers air conditioning, Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, a swimming pool, a balcony with sea views, and on-site parking, with massage services and a fitness centre also available.
One Ocean - B 1103 - Siesta Key, FL
9.2 382 reviews
Siesta Key, FL
22/08 – 05/09
132 €/nighttotal: 1848 € (14 )

One Ocean - B 1103

2 3
house , Siesta Key
This Siesta Key holiday home is just a short walk from Crescent Beach and a little over a mile from Turtle Beach, making it ideal for beach lovers seeking a relaxing escape. It has received excellent ratings for location, cleanliness and overall user experience.
The two-bedroom house offers 91 square metres of living space and features a fully equipped kitchen, a comfortable living room, and a private terrace. Amenities include air conditioning, a dishwasher, a TV with cable channels, a spa, a garden, and parking.
The Beach Club At Siesta #100d - Siesta Key, FL
9.0 2 reviews
Siesta Key, FL
23/06 – 30/06
275 €/nighttotal: 1925 € (7 )

The Beach Club At Siesta #100d

1 2
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.

Best Siesta Key, FL villas and holiday homes with jacuzzi

6415 Midnight Pass #605 - Siesta Key, FL
8.0 1 review
Siesta Key, FL
12/07 – 19/07
341 €/nighttotal: 2387 € (7 )

6415 Midnight Pass #605

2 5
house , Siesta Key
This Siesta Key holiday home, 6415 Midnight Pass #605, is a short 1.1km walk from Crescent Beach and within 2.6km and 4.8km of Turtle Beach and Siesta Key Beach respectively, offering convenient access to these popular locations.
The 116 square metre property boasts two bedrooms, two bathrooms, sleeping up to eleven guests, and includes a private swimming pool, jacuzzi, sauna, fitness centre, and tennis court, alongside a fully equipped kitchen and free Wi-Fi.
New Listing - Dates Available Now! Beach & Village, Pool, Dock, Game Room! - Siesta Key, FL
Siesta Key, FL
30/07 – 05/08
476 €/nighttotal: 2856 € (6 )

New Listing - Dates Available Now! Beach & Village, Pool, Dock, Game Room!

1 2
house , Siesta Key
This Siesta Key holiday cottage offers a prime location, just a 5-minute walk to Siesta Key Beach and 16 kilometres from the John and Mable Ringling Museum of Art.
This property accommodates up to four guests and features a private dock, a game room, a fitness room, a patio, a swimming pool, and a children's playground, with a kitchen equipped with a fridge, microwave oven, and toaster.
The Lookout - Siesta Key, FL
Siesta Key, FL
04/07 – 08/07
3469 €/nighttotal: 13876 € (4 )

The Lookout

5 4
house , Siesta Key
This five-bedroom Siesta Key holiday home is a two-minute walk from Siesta Key Beach and 1.3 kilometres from Crescent Beach, offering easy access to Sarasota's attractions within a 16-kilometre radius.
The 418-square-metre property boasts a spacious layout with two living rooms, accommodating up to 16 guests, and includes a private swimming pool, Jacuzzi, and terrace with pool views, alongside free Wi-Fi and concierge service.
321 M² House ∙ 5 Bedrooms ∙ 13 Guests - Siesta Key, FL
9.9 16 reviews
Siesta Key, FL
04/07 – 11/07
816 €/nighttotal: 5712 € (7 )

321 M² House ∙ 5 Bedrooms ∙ 13 Guests

5 4
house , Siesta Key
This waterfront villa provides direct navigable canal access to the Gulf of Mexico, located a mere 120 metres from Siesta Beach, the United States' top-rated beach.
This expansive 321 square metre property accommodates up to 13 guests across five bedrooms, featuring a private screened enclosure with a pool, hot tub, and BBQ area, alongside convenient access to Siesta Key Village via the local trolley service.
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