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.

Relax In This 2 Bed, 2 Bath Condo With A Partial North View In Beautiful Sarasota! - Siesta Key, FL
9.6 50 reviews

Relax In This 2 Bed, 2 Bath Condo With A Partial North View In Beautiful Sarasota!

apartment, Siesta Key
This Siesta Key condo rental boasts partial Gulf views from its 10th-floor location, offering close proximity to Siesta Key Beach and Turtle Beach, with St. Armands Circle and the Mall at University Town Center a short drive away.
This 1,300-square-foot apartment features two bedrooms (king and two queen beds), two bathrooms, and accommodates up to six guests, complete with a fully equipped kitchen, in-unit laundry, a swimming pool, and free parking.

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.

Best Value 2br  Walk To Beach, Dining & Nightlife - Siesta Key, FL
9.8 18 reviews

Best Value 2br Walk To Beach, Dining & Nightlife

apartment, Siesta Key
This Siesta Key beachfront rental is less than a mile from Crescent Beach and Siesta Key Beach, and two miles from Turtle Beach, offering easy access to three of the island's most popular stretches of sand.
The two-bedroom, one-bathroom condo sleeps eight guests comfortably, features a fully equipped kitchen with a refrigerator and microwave, a private balcony, free Wi-Fi, and on-site parking.

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.

110 M² Condo ∙ 2 Bedrooms ∙ 5 Guests - Siesta Key, FL
No reviews

110 M² Condo ∙ 2 Bedrooms ∙ 5 Guests

apartment, Siesta Key
This 2-bedroom, 2-bathroom condo offers direct access to a private beach on Siesta Key, located in a district with convenient proximity to dining and shopping.
This 1180 sq ft residence accommodates up to 5 guests and features a fully-equipped kitchen, WiFi, air conditioning, a private screened lanai with ocean views, and access to a heated pool and tennis courts, with biking and watersports nearby.
Gertrude's Siesta | Oceanview, 1-min To Beach - Siesta Key, FL
9.7 196 reviews

Gertrude's Siesta | Oceanview, 1-min To Beach

apartment, Siesta Key
This Siesta Key apartment rental is conveniently located less than a mile from Siesta Key Beach, the Siesta Key Beach Playground, and the Siesta Key Farmers Market.
The three-bedroom, two-bathroom unit sleeps up to 10 guests and boasts a fully equipped kitchen, private terrace, swimming pool, on-site water park, and barbecue grills, perfect for families or large groups.
Beach Rd, 300ft To Beach Access & 500ft To Siesta Key Village, Studio - Siesta Key, FL
9.8 60 reviews

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

apartment, Siesta Key
This studio condo in Siesta Key is located directly across from Siesta Key Beach, with beach access just 100 steps away, and is a 5-minute walk from Siesta Village.
This apartment offers a queen bed, a private porch, a full kitchen with a fridge and microwave, complimentary WiFi, and includes beach essentials, with one private parking space.
119 M² Condo ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
9.3 3 reviews

119 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Siesta Key
This 2-bedroom condo in Siesta Key is located directly across from Crescent Beach, a 1280 square foot unit with a full-width balcony offering picturesque views, and is within a 10-minute walk to Siesta South Village's market and dining. Guests can enjoy amenities at The Anchorage Yacht and Tennis Club, including a heated Olympic-sized pool and fitness center, with free boat docking available on the Inter-Coastal Waterway and private gated access to the beach.

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.

2-bedroom 2-bathroom Condominium Is Located On The Bay Side Of Our Property. - Siesta Key, FL
9.8 51 reviews

2-bedroom 2-bathroom Condominium Is Located On The Bay Side Of Our Property.

apartment, Siesta Key
This newly renovated, first-floor condo on the Bay side of Siesta Key offers a short, approximately 0.2-mile walk to the Gulf side's beach and is conveniently located 3 miles from St. Armands Circle and 5 miles from Mote Marine Laboratory & Aquarium.
This 1090 square feet apartment accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, and a private outdoor patio, with parking available.

Best Siesta Key, FL lodging with a balcony

Newly Remodeled Apt! Key-west Victorian With Beach Access, To Siesta Key Beach! - Siesta Key, FL
8.8 4 reviews

Newly Remodeled Apt! Key-west Victorian With Beach Access, To Siesta Key Beach!

apartment, Siesta Key
Gertrude Siesta | Patio | 15-min Beach! - Siesta Key, FL
9.7 183 reviews

Gertrude Siesta | Patio | 15-min Beach!

apartment, Siesta Key
Cozy 1-bedroom 2 Full Bath Condo In Peaceful Siesta Key .55 & Over,1 Month Stay. - Siesta Key, FL
No reviews

Cozy 1-bedroom 2 Full Bath Condo In Peaceful Siesta Key .55 & Over,1 Month Stay.

apartment, Siesta Key
Best Deal On Siesta Key!  Priced Below Market 1/1 Full Views Sunsets/ Beach - Siesta Key, FL
10 2 reviews

Best Deal On Siesta Key! Priced Below Market 1/1 Full Views Sunsets/ Beach

apartment, Siesta Key

Best Siesta Key, FL lodging with a kitchen

Amazing Siesta Key Condo In Midnight Cove Ii - Siesta Key, FL
9.3 91 reviews

Amazing Siesta Key Condo In Midnight Cove Ii

apartment, Siesta Key
Trendy & Fun Haven: Walk To Beach ~ Jacuzzi ~ Pool - Siesta Key, FL
8.8 13 reviews

Trendy & Fun Haven: Walk To Beach ~ Jacuzzi ~ Pool

apartment, Siesta Key
Charming Siesta Key Village Vacation Condo - Unbeatable Location, Free Wifi - Siesta Key, FL
9.2 96 reviews

Charming Siesta Key Village Vacation Condo - Unbeatable Location, Free Wifi

apartment, Siesta Key
Beautiful Spacious Condo On Siesta Key! - Siesta Key, FL
9.8 26 reviews

Beautiful Spacious Condo On Siesta Key!

apartment, Siesta Key

Best Siesta Key, FL lodging with laundry available

Siesta Key Beach - Bari 665 #2 - Siesta Key, FL
8.9 316 reviews

Siesta Key Beach - Bari 665 #2

apartment, Siesta Key
Siesta Key Dream Vacation - Siesta Key, FL
9.7 196 reviews

Siesta Key Dream Vacation

apartment, Siesta Key
Siesta Gardens @ Siesta Key Village - Siesta Key, FL
9.9 448 reviews

Siesta Gardens @ Siesta Key Village

apartment, Siesta Key
Jamaica Royale Villa: Modern 1br Retreat  Sleeps 6 With Private Beach Access And Vip Perks Daily! - Siesta Key, FL
9.6 58 reviews

Jamaica Royale Villa: Modern 1br Retreat Sleeps 6 With Private Beach Access And Vip Perks Daily!

apartment, Siesta Key
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