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 air conditioning

The Beach Club At Siesta #103e - Siesta Key, FL
8.0 1 review

The Beach Club At Siesta #103e

house, Siesta Key
This beachfront holiday home in Point O'Rocks offers direct access to Crescent Beach and is located 17.7 kilometres from the John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 65 square metre, two-bedroom holiday home accommodates up to 11 guests and features a fully equipped kitchen, a patio, a heated swimming pool, a hot tub, a fitness centre, and facilities for guests with disabilities, with WiFi and private parking also provided.
Gulf View Suite - 301 - Siesta Key, FL
No reviews

Gulf View Suite - 301

house, Siesta Key
This Gulf View Suite is located in Siesta Key, a 1-minute walk from Crescent Beach and approximately 12 kilometres from Marina Jack Restaurant and Marina, and Sarasota Opera.
This accommodation offers direct beach access, sea views, a fully equipped kitchen, a fireplace, air conditioning, a washing machine, a lift, and outdoor barbecue facilities for up to 19 guests.
Salty Manor Estate - Siesta Key, FL
No reviews

Salty Manor Estate

house, Siesta Key
This large house in Siesta Key is a 5-minute walk from Crescent Beach and 17.7 kilometres from Sarasota Bradenton International Airport and the John and Mable Ringling Museum of Art.
This property boasts a floor area of 836 square meters, accommodates up to 80 guests with 17 bathrooms, and offers an on-site casino, spa centre, water park, outdoor swimming pool, garden, and patio with lake views, all with free WiFi and air conditioning.
Minorga Sand Dollar On The Key - Siesta Key, FL
9.5 129 reviews

Minorga Sand Dollar On The Key

house, Siesta Key
Minorga On the Key is located just 800 metres from Siesta Key Beach and 2.4 kilometres from Crescent Beach, with the John and Mable Ringling Museum of Art 15 kilometres away and Sarasota Opera 10 kilometres away. The property has received excellent ratings for location, cleanliness and overall experience.
The house features a well-equipped kitchen with a fridge, microwave oven, and dishwasher, as well as a comfortable seating area. This Siesta Key holiday home also offers free Wi-Fi, satellite TV, a washing machine, air conditioning, a private swimming pool, a garden, and private parking.

Our Favourite Holiday Homes with a Hot Tub in Siesta Key, FL

Whether you prefer a jacuzzi or a hot tub, these holiday homes in Siesta Key, FL offer a private setting for a relaxing soak.

Top Gulf - Siesta Key, FL
9.9 15 reviews

Top Gulf

house, Siesta Key
Top Gulf, a Siesta Key holiday home, enjoys a prime location a 0.5km stroll from Siesta Key Beach and under 1.6km from Crescent Beach.
This self-catering property offers free private parking, a fully equipped kitchen including dishwasher, air conditioning, a private swimming pool and jacuzzi, plus free Wi-Fi and satellite TV; nearby attractions include Marina Jack, the Sarasota Opera House, and the Ringling Museum of Art.
New Listing - Dates Available Now! Beach & Village - Siesta Key, FL
No reviews

New Listing - Dates Available Now! Beach & Village

house, Siesta Key
This Siesta Key bungalow is situated a 5-minute walk from Siesta Key Beach, 16 kilometres from the John and Mable Ringling Museum of Art, and 19 kilometres from Sarasota International Convention Centre.
This property offers accommodation for up to four guests, featuring one bedroom, one bathroom, air conditioning, Wi-Fi, a kitchen with a fridge and microwave, a swimming pool, a hot tub, and a garden, with a fitness centre and parking also available.
Palm Bay Gulf Side - Siesta Key, FL
9.6 123 reviews

Palm Bay Gulf Side

house, Siesta Key
Palm Bay Gulf Side, a Siesta Key holiday home, is situated a short walk from Crescent Beach and 1.8km from Siesta Key Beach, offering easy access to both.
This 121 square metre property boasts a fully equipped kitchen, private parking, a swimming pool, Jacuzzi, and fitness centre, alongside proximity to Sarasota attractions such as the Sarasota Opera House and The Ringling.
Siesta Key Village, Pool, Beach Access 4-min Walk - Siesta Key, FL
9.6 61 reviews

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

house, Siesta Key
This three-bedroom Siesta Key townhouse is situated in Siesta Key Village, a mere 0.016km from shops and restaurants, and a 0.8km stroll from Siesta Beach.
Sleeping up to ten guests, this property boasts a shared heated pool, BBQ area, fully equipped kitchen with stainless steel appliances, free high-speed internet, and beach essentials; optional add-ons include mid-stay cleaning and golf cart rental.

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 famous for its beautiful beaches, so you'll want to spend some time on Siesta Key Beach, voted one of the best beaches in the USA. You can also visit the Siesta Key Drum Circle, a vibrant gathering of musicians and performers. If you want to explore further, you can take a trip to the nearby Sarasota Jungle Gardens, a tropical oasis with exotic animals and lush vegetation.
  • What are the best holiday homes in Siesta Key, FL?

    Among the holiday homes 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 around Siesta Key, like herons, egrets, and pelicans. You might also spot dolphins playing in the Gulf of Mexico, and if you're lucky, you might even see a manatee or two in the waters around the key.
  • What are the best holiday homes 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 holiday homes 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 good but the crowds are smaller and prices are lower. You'll also find the weather more pleasant than during the hot and humid summer months.
  • What are the best holiday homes with a jacuzzi in Siesta Key, FL?

  • What are the top hiking trails near Siesta Key, FL?

    There aren't many hiking trails directly on Siesta Key, but you can find some great trails nearby at Myakka River State Park, about a 45-minute drive from the key. There, you can explore the diverse ecosystems of the park, including the Myakka River, a beautiful cypress swamp, and a pine flatwoods.
  • What are the best holiday homes for families and kids in Siesta Key, FL?

    The best holiday homes 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 advantages of renting a house or a villa in Siesta Key, FL

    Renting a villa in Siesta Key offers more space and privacy than a hotel room. You'll also have access to a kitchen and laundry facilities, which can be convenient for families or groups travelling together. You can also often find villas with private pools or other amenities that you won't find in a hotel.
  • What are the best pet friendly holiday homes in Siesta Key, FL?

  • Are there popular destinations near Siesta Key, FL?

    Yes, there are plenty of popular destinations near Siesta Key. Sarasota is just a short drive away and offers a vibrant downtown area with shops, restaurants, and museums. You can also visit the Ringling Museum of Art, the Mote Marine Laboratory & Aquarium, and the Marie Selby Botanical Gardens, all within easy reach of Siesta Key.
  • What are the best holiday homes with parking in Siesta Key, FL?

    Crescent Beach 1011 #1, Across The Street From #1 Beach and Siesta Key Beachside Villas are the best holiday homes with parking in Siesta Key, FL.

Popular destinations

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

086tower East View - Siesta Key, FL
No reviews

086tower East View

house, Siesta Key
This apartment is located in the Grande Tower Building, offering direct access to Siesta Key's quartz sand beaches and the Gulf waters, just a short walk away.
This property accommodates up to four guests with one bedroom and one bathroom, featuring a combined living and dining area, a galley kitchen, a patio overlooking the Gulf, and amenities such as a Jacuzzi, spa, and tennis court.
Harbor Tower Intracoastal Condo - Siesta Key, FL
9.8 33 reviews

Harbor Tower Intracoastal Condo

house, Siesta Key
This Siesta Key property is located just a short walk from Crescent Beach and less than 1.6 km from Siesta Key Beach, offering easy access to the area's beautiful white sand beaches. The property has excellent user ratings for cleanliness, location and overall experience.
The 163 square metre house provides comfortable accommodation for a family or group of friends. It boasts a fully equipped kitchen, a terrace, a garden, a swimming pool, a tennis court, and a range of other amenities, making it perfect for a relaxing and enjoyable stay.
Private Beach Retreat On Siesta Key! Bright Villa - Siesta Key, FL
10 14 reviews

Private Beach Retreat On Siesta Key! Bright Villa

house, Siesta Key
This 2-bedroom, 2-bathroom villa offers direct private access to Siesta Key Beach and is conveniently located near Siesta Village, approximately 1.6 kilometres away, with a trolley stop on-site for easy transport.
Guests can enjoy a private lanai, outdoor seating, a communal heated pool, a game room, and included beach chairs, with the single-storey accommodation designed for ease of access and a capacity of 6 people.
Serenity Cottage - 1028 - Siesta Key, FL
9.0 2 reviews

Serenity Cottage - 1028

house, Siesta Key
Serenity Cottage - 1028 is a three-bedroom, three-bathroom property situated in Siesta Key, Florida, a two-minute walk from Crescent Beach and 1.8km from Turtle Beach.
This 191 square metre holiday home sleeps up to 15 guests and boasts a private pool, spa, free Wi-Fi, and free parking, plus a fully equipped kitchen and satellite TV.

Best Holiday Houses with a Swimming Pool in Siesta Key, FL

On-site pool access at your holiday home in Siesta Key, FL makes a refreshing dip the perfect way to complement a day by the water.

Sun And Sea Vaccations - Siesta Key, FL
9.5 2 reviews

Sun And Sea Vaccations

house, Siesta Key
This holiday rental in Sarasota offers direct access to a private beach area, just 200 metres from Crescent Beach.
This air-conditioned villa features a swimming pool, WiFi, private parking, a balcony and a fully equipped kitchen, ideal for families visiting Siesta Key.
Heat Of Siesta Village Walk To Beach W Heated Pool - Siesta Key, FL
9.7 162 reviews

Heat Of Siesta Village Walk To Beach W Heated Pool

house, Siesta Key
This Siesta Key holiday home is a seven-minute walk from Siesta Key Beach and within 10-16km of attractions including the Ringling Museum, Sarasota Opera House, and St. Armands Circle.
The 71 square metre property offers two bedrooms, one bathroom, a private heated pool, fully equipped kitchen, and free Wi-Fi; sleeping up to four guests comfortably.
Charming Beach Bungalow With Private Pool And Steps Away From The Beach! - Siesta Key, FL
10 154 reviews

Charming Beach Bungalow With Private Pool And Steps Away From The Beach!

cottage, Sarasota
This pet-friendly holiday home in Sarasota offers a strategic waterfront position, just a 13-minute walk from the boutiques and eateries of St. Armands Circle and close to Lido Beach for watersports.
Guests can enjoy a well-equipped kitchen with a microwave and dishwasher, air conditioning, a swimming pool, spa, and on-site barbecue, with Wi-Fi, a TV, washer, dryer, linens, and towels provided.
Siesta Key - Private Beach Access - 2br Retreat - Siesta Key, FL
9.7 115 reviews

Siesta Key - Private Beach Access - 2br Retreat

house, Siesta Key
This Siesta Key condo boasts private beach access, requiring no road crossings, and is a short walk from the free trolley stop, offering easy exploration of the island.
Sleeping eight guests, this two-bedroom, one-bathroom property features a well-equipped kitchen, a private pool, and provides beach chairs and loungers, plus charcoal grills for guest use.

Top-Rated Coastal Holiday Homes in Siesta Key, FL

Base your next maritime trip at comfortable coastal holiday homes located a short distance from beaches in Siesta Key, FL.

Sun N Sea #1 - Siesta Key, FL
No reviews

Sun N Sea #1

house, Siesta Key

Choose the Right 5-Star Holiday Houses in Siesta Key, FL

A luxury holiday home in Siesta Key, FL provides a spectacular setting for your break, delivering 5-star comfort and breathtaking views throughout your stay.

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

[Beach Elements] Pool View Withprivate Beach Access

house, Siesta Key

Top Family-Friendly Holiday Homes in Siesta Key, FL

Choosing the right holiday home makes all the difference for a family trip to Siesta Key, FL, offering ample room.

311 M² House ∙ 4 Bedrooms ∙ 12 Guests - Siesta Key, FL
9.9 29 reviews

311 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Siesta Key
Serene Bay Front Condo On Siesta Key - 2 Heated Pools, Pickleball And Tennis, Private Beach Access - Siesta Key, FL
10 2 reviews

Serene Bay Front Condo On Siesta Key - 2 Heated Pools, Pickleball And Tennis, Private Beach Access

house, Siesta Key
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
120 M² House ∙ 3 Bedrooms ∙ 6 Guests - Siesta Key, FL
No reviews

120 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Siesta Key

Top-Rated Dog-Friendly Holiday Houses in Siesta Key, FL

Your dog-friendly holiday home in Siesta Key, FL ensures easy beach access and handy outdoor taps.

Sandbar Social - Siesta Key, FL
No reviews

Sandbar Social

house, Siesta Key
Casa Junonia - 1032l - Siesta Key, FL
9.4 5 reviews

Casa Junonia - 1032l

house, Siesta Key
Casa Stolida - 1030l - Siesta Key, FL
10 1 review

Casa Stolida - 1030l

house, Siesta Key
Private Beach. Rock Wall. Pool W/ Zip Line & Slide - Siesta Key, FL
No reviews

Private Beach. Rock Wall. Pool W/ Zip Line & Slide

house, Siesta Key

Check Out Holiday Homes with Parking in Siesta Key, FL

On-site parking removes one more worry from your list, as these holiday homes in Siesta Key, FL include dedicated spaces for a stress-free arrival.

Siesta Key Village, Pool, Beach Access 4-min. Walk, 3bdr - Siesta Key, FL
10 6 reviews

Siesta Key Village, Pool, Beach Access 4-min. Walk, 3bdr

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

The Beach Club At Siesta #106c

house, Siesta Key
Villa 5, Siesta Key, Pool View. King Bed. Daily Rentals - Siesta Key, FL
9.6 444 reviews

Villa 5, Siesta Key, Pool View. King Bed. Daily Rentals

hotel, Siesta Key
Large Home, Private Pool, Arcade Lounge And Beach - Siesta Key, FL
No reviews

Large Home, Private Pool, Arcade Lounge And Beach

house, Siesta Key
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