Siesta Key, FL Short term rentals

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Siesta Key, FL short term rentals
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Best Short term and Weekly rentals in Siesta Key, FL

Top-Rated Oceanfront Short-Term Rentals in Siesta Key, FL

Experience relaxing maritime vibes at coastal short-term rentals in Siesta Key, FL, situated short distances from regional beach-town boardwalks.

Casita Mar | Pet Friendly, Siesta Key Home With Pool & Beach Access Included! - Siesta Key, FL
9.6 43 reviews

Casita Mar | Pet Friendly, Siesta Key Home With Pool & Beach Access Included!

apartment, Siesta Key
This Siesta Key beachfront home is located near Crescent Beach and Siesta Key Beach, less than 1.2 miles away, and 2.1 miles from Turtle Beach.
This pet-friendly vacation rental boasts a private hot tub, fully equipped kitchen, in-unit laundry, access to a communal water park, barbecue grills, and a pool, jacuzzi, and spa.

Our Favorite Luxury Short-Term Rentals in Siesta Key, FL

Experience the pinnacle of comfort in Siesta Key, FL with a luxury rental designed to meet your every need.

Siesta Key Familygetaway!! - Siesta Key, FL
10 98 reviews

Siesta Key Familygetaway!!

apartment, Siesta Key
This Siesta Key vacation home sits less than a mile from Siesta Key Beach, near St. Boniface Episcopal Church Labyrinth and under two miles from Siesta Key Beach Playground and Irma Beach.
This 1980-square-foot house features four bedrooms, three bathrooms, sleeps eight, and includes a private pool, outdoor grills, and free Wi-Fi.

Frequently Asked Questions about short term rentals in Siesta Key, FL

  • Which top landmarks shouldn't you miss in and around Siesta Key, FL?

    You have to visit Siesta Key Beach, known for its soft, white sand and clear water. The Siesta Key Drum Circle on Sundays is a fun experience, and the historic Siesta Key Village is a must-see for shopping and dining.
  • What are the best short term rentals in Siesta Key, FL?

  • What types of short-term rentals are available in Siesta Key?

    When you are thinking of holidays in Siesta Key you would want to look for the best short-term rentals which would make things easier for you. This is important because you want to stay with your family and pet in a private space. Short-term rentals like condos, apartments and lofts and even townhouses provide you with the best private space you need when you are visiting Siesta Key. Choosing short-term rentals would also allow you to live in different neighbourhoods to make your stay convenient. If you are travelling with a pet you can make use of these rental properties which are pet-friendly and come with additional kitchen and bathroom facilities and amenities.
  • What notable natural landmarks are near Siesta Key, FL?

    Myakka River State Park is a beautiful place to go kayaking or hiking. The nearby Sarasota Jungle Gardens has a variety of exotic animals and plants. And, of course, there's the Gulf of Mexico, perfect for swimming, sunbathing, and fishing.
  • What are the best short term rentals with a pool in Siesta Key, FL?

  • What are the best kid-friendly attractions in Siesta Key?

    1. Siesta Key Beach - When you are in Siesta Key you would want to visit Siesta Key Beach with your kids where they can have a fun day playing in the sand and enjoying the sea.
    2. Mote Marine Laboratory and Aquarium - Taking your kids to an aquarium is a great way to spend a holiday. While this is a non-profit laboratory you can also find an aquarium featuring many marine animals and plant life.
    3. Siesta Key Village - When you have kids you can head to Siesta Key Village where you can shop and dine with the kids and take them to one of the many ice cream shops in the village.
  • What family-friendly activities are available near Siesta Key, FL?

    The Siesta Key Beach is perfect for families with its shallow waters and soft sand. The Mote Marine Laboratory & Aquarium is a great place to learn about marine life. You can also visit the Sarasota County Fairgrounds for fun events and activities.
  • What are the best short term rentals with a jacuzzi in Siesta Key, FL?

  • What is the best neighbourhood to stay close to the city centre?

    If you prefer to stay close to the city centre you would want to look for accommodations in Reigels Landing which allows you to be just minutes away from the popular Siesta Key Beach. This means you can access the beach facilities and spend a day without having to commute much. Also, being here allows you to move around the island quickly and also access Stickney Point Road and explore Sarasota. Staying in Riegels Landing also allows you to enjoy the best local restaurants, bars and clubs close to the beach.
  • What kind of weather can travelers expect in Siesta Key, FL?

    Siesta Key has a subtropical climate with hot, humid summers and mild, dry winters. The average high temperature in July is around 90 degrees Fahrenheit, and the average low temperature in January is around 55 degrees Fahrenheit. You can expect sunshine most of the year.
  • What are the best short term rentals for families and kids in Siesta Key, FL?

  • What are the best shopping malls in Siesta Key?

    1. Southbridge Mall - If you are somewhere around Turtle Beach you can shop at the Southbridge Mall which has a good selection of shopping stores in Siesta Key.
    2. Sarasota Pavilion - When you are in Siesta Key you can also shop at the Sarasota Pavilion which is in Sarasota but close to Siesta Key. If you are looking for discount shopping and groceries this is where you can find the right options.
    3. Southbridge Plaza - When you intend to shop in Siesta Key you can head to Southbridge Plaza where you can find plenty of stores to shop on discounts.
  • What major cities can be found near Siesta Key, FL?

    Siesta Key is located just south of Sarasota, a vibrant city with a thriving arts and culture scene. You can also easily reach St. Petersburg and Tampa, which are both about an hour's drive away.
  • What is the best place to book a short-term rental for the Siesta Key Crystal Classic International Sand Sculpting Festival in Siesta Key?

    If you are planning to stay in Siesta Key for Siesta Key Crystal Classic International Sand Sculpting Festival you should look for short-term rentals in and around Riegels Landing. This would allow you to make the most of your accommodation. With plenty of short-term rentals in this area, you can choose from multiple condos, apartments and townhouses. Also, staying in the Riegels Landing neighbourhood would allow you to access Siesta Key Beach and various restaurants, cafes, bars and clubs around the beach. If you are looking for nightlife activities you can find plenty of venues here. With the best rental properties, you can stay privately and comfortably in Siesta Key and visit the event.

Popular destinations

Choose the Right Family-Friendly Lodgings in Siesta Key, FL

Perfect for families, these Siesta Key, FL short-term rentals offer coastal comfort and quick access to the shore.

Gertrude Siesta | Patio | 15-min Beach! - Siesta Key, FL
9.7 177 reviews

Gertrude Siesta | Patio | 15-min Beach!

apartment, Siesta Key
This family-friendly vacation rental is located just a mile from Irma Beach and Siesta Key Beach, making it a perfect choice for those who want to be close to the action. The property consistently receives excellent ratings for cleanliness, location, and overall experience.
This 3-bedroom, 3-bathroom home comfortably accommodates up to 10 guests. Enjoy features such as a private pool, a tennis court, and a fully equipped kitchen, allowing you to relax and enjoy your vacation to the fullest.
Beautiful 2025 Renovated - 550 Sq Ft  Patio - Across Street From Beach - Siesta Key, FL
9.2 40 reviews

Beautiful 2025 Renovated - 550 Sq Ft Patio - Across Street From Beach

apartment, Siesta Key
This beachfront condo rental on Siesta Key is a short walk from St. Boniface Episcopal Church Labyrinth and Siesta Key Beach, and within two miles of Crescent Beach and Siesta Key Beach Playground.
This 1770-square-foot Siesta Key vacation rental boasts two bedrooms, two bathrooms, accommodates six guests, and features a private pool, fully equipped kitchen, balcony, and access to a fitness center, sauna, and tennis court.
Gertrude Siesta | Oceanview 1-min To Beach! - Siesta Key, FL
9.7 6 reviews

Gertrude Siesta | Oceanview 1-min To Beach!

apartment, Siesta Key
This Siesta Key vacation rental, located on Beach Road in Siesta Key Village, offers three renovated apartments—13 steps from Beach Access 10 and a one-minute trolley ride from shops and restaurants.
Three spacious apartments, ranging from one to three bedrooms and accommodating up to 16 guests, feature fully equipped kitchens, air conditioning, and beach access; pet-friendly with a fee, they also provide beach chairs and towels.
Gertrude's Siesta | Bayview Unit W/ Balcony, Pools & Private Beach! - Siesta Key, FL
9.2 33 reviews

Gertrude's Siesta | Bayview Unit W/ Balcony, Pools & Private Beach!

apartment, Siesta Key
This Siesta Key waterfront rental is located less than a mile from Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offering easy access to prime Siesta Key attractions.
This 1,000-square-foot apartment features three bedrooms, two bathrooms, and sleeps eight guests, boasting a fully equipped kitchen, free Wi-Fi, a private terrace, and access to a swimming pool, fitness center, and tennis court.

Neighborhoods and points of interest in Siesta Key, FL

Discover Pet-Friendly Short-Term Rentals in Siesta Key, FL

Forget the post-beach mess; these short-term rentals in Siesta Key, FL feature dog-friendly amenities.

Available For Season! Tequila Sunrise On Siesta Key - Siesta Key, FL
9.7 3 reviews

Available For Season! Tequila Sunrise On Siesta Key

apartment, Siesta Key
This vacation rental is situated in Sarasota's Siesta Key district, just a 3-minute walk from Crescent Beach and 11 miles from The John and Mable Ringling Museum of Art.
This 1710 square foot condo accommodates up to 11 guests, featuring 2 bathrooms, a full kitchen with a dishwasher and oven, complimentary WiFi, air conditioning, a terrace, and access to a spa and fitness center, with on-site parking available.

Best Siesta Key, FL lodging with a balcony

Midnight Cove #714, Bayside In Siesta Key, Fl, 2br-1 1/2ba, 1st Floor - Siesta Key, FL
8.9 47 reviews

Midnight Cove #714, Bayside In Siesta Key, Fl, 2br-1 1/2ba, 1st Floor

apartment, Siesta Key
Siesta Beach Getaway With Heated Pool - Siesta Key, FL
No reviews

Siesta Beach Getaway With Heated Pool

apartment, Siesta Key
Summer House | Walk To Beach & Siesta Key Village - Siesta Key, FL
10 2 reviews

Summer House | Walk To Beach & Siesta Key Village

apartment, Siesta Key
Key West Villa 3 Min To #1 Beach • Pool • Bbq - Siesta Key, FL
9.1 11 reviews

Key West Villa 3 Min To #1 Beach • Pool • Bbq

apartment, Siesta Key

Best Siesta Key, FL lodging with a kitchen

Aqua Oasis- Tiny House Sleeps 4 & Pet Friendly - Siesta Key, FL
9.0 107 reviews

Aqua Oasis- Tiny House Sleeps 4 & Pet Friendly

house, Gulf Gate Estates
Fully Renovated Condo On Bay | Resort Amenities - Siesta Key, FL
9.7 6 reviews

Fully Renovated Condo On Bay | Resort Amenities

apartment, Siesta Key
Siesta Beach 3 Min | Walk To Village + Patio! - Siesta Key, FL
10 5 reviews

Siesta Beach 3 Min | Walk To Village + Patio!

apartment, Siesta Key
Vinca | Steps To Siesta Key Village! - Siesta Key, FL
9.5 110 reviews

Vinca | Steps To Siesta Key Village!

apartment, Siesta Key

Best Siesta Key, FL lodging with laundry available

1 Min Walk To Beach Path | Walk To Dining & Music - Siesta Key, FL
9.5 31 reviews

1 Min Walk To Beach Path | Walk To Dining & Music

apartment, Siesta Key
Experience Serenity In This 2br, 2ba Condo At Bayside, Sarasota. - Siesta Key, FL
9.6 52 reviews

Experience Serenity In This 2br, 2ba Condo At Bayside, Sarasota.

apartment, Siesta Key
New! Beachside Bungalow | Entire Duplex, Walk To Crescent Beach, And Community Pool - Siesta Key, FL
No reviews

New! Beachside Bungalow | Entire Duplex, Walk To Crescent Beach, And Community Pool

apartment, Siesta Key
Mimosa | Steps From Beach & Siesta Key Village! - Siesta Key, FL
9.6 10 reviews

Mimosa | Steps From Beach & Siesta Key Village!

apartment, Siesta Key
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