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.

Siesta Key Walkout Beachfront Condo - Siesta Key, FL
9.9 76 reviews

Siesta Key Walkout Beachfront Condo

apartment, Siesta Key
This ground-floor condo at Crescent Royale on Siesta Key offers direct access to the world-famous Siesta Beach.
The two-bedroom, two-bathroom unit sleeps six, features a screened lanai with Gulf sunset views, updated appliances, and dedicated carport parking, plus access to the community pool, fitness center, and more.

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.

Renovated Condo Across From Siesta Key Beach | Heated Pool | Dogs Welcome - Siesta Key, FL
No reviews

Renovated Condo Across From Siesta Key Beach | Heated Pool | Dogs Welcome

apartment, Siesta Key
This dog-friendly condo in White Sands Village is located directly across from Siesta Key Beach, a short walk or drive to the sand, and offers convenient proximity to Siesta Key Village's shops and dining.
This 1080 sq ft, 2-bedroom, 2-bathroom unit accommodates up to 4 guests and features a screened lanai, a heated community pool, BBQ grills, and includes assigned covered parking, daily activities, and airport transportation through the Xplorie program.

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.

Sundeck With Ocean View, Private Access To Beach & 500ft To The Village - Siesta Key, FL
No reviews

Sundeck With Ocean View, Private Access To Beach & 500ft To The Village

apartment, Siesta Key
This Siesta Key condo offers direct private beach access, just 20 steps from the quartz sand, and is a 3-minute walk to Siesta Village's dining, shopping, and entertainment.
This family-friendly 3-bedroom, 2-bathroom residence accommodates up to 10 guests with 7 beds, featuring a private balcony with partial ocean views, a shared rooftop deck, complimentary high-speed internet, and two reserved parking spaces.
Beautiful Large Home Bike To Siesta Key, Quiet Neighborhood With Local Owners! - Siesta Key, FL
9.8 61 reviews

Beautiful Large Home Bike To Siesta Key, Quiet Neighborhood With Local Owners!

apartment, Siesta Key
This Siesta Key house is located just two miles from the beach and a short bike ride from the vibrant downtown area. It's rated excellent by previous guests, so you can be sure of a comfortable stay. This 3,000 square foot home has three bedrooms and three bathrooms, comfortably accommodating up to eight guests. The house features a fully equipped kitchen, a private spa, a spacious terrace, and a beautiful garden, perfect for relaxing after a day at the beach.
Gertrude's Siesta | 8-steps To Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets - Siesta Key, FL
10 3 reviews

Gertrude's Siesta | 8-steps To Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets

apartment, Siesta Key
This Siesta Key rental is conveniently located less than a mile from Crescent Beach and Siesta Key Beach, and about two miles from Turtle Beach, offering easy access to three of the island's most popular beaches.
This three-bedroom, two-bathroom condo sleeps twelve guests and boasts a fully equipped kitchen, free WiFi, a private terrace, a swimming pool, a fitness center, and on-site water park amenities.
Siesta Key Beachside Villas - Siesta Key, FL
8.9 1785 reviews

Siesta Key Beachside Villas

house, Siesta Key
The Siesta Key Beachside Villas are located just a short 2-minute walk from the renowned Siesta Key Beach, offering direct access to the powdery white sands and turquoise waters. The villas have received very good user ratings, excellent location ratings, and very good cleanliness ratings. Each unit features a private bathroom, Keurig coffee maker, refrigerator, and microwave, with some offering full kitchens for self-catering. Guests can enjoy the outdoor pool, relax in a hammock, gather around the barbecue facilities, and access the pool at the nearby Siesta Beach Resorts and Suites.

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.

Ground-floor Condo With Community Pool And Beach Access - Sea Club Ii Unit 2b - Siesta Key, FL
8.8 12 reviews

Ground-floor Condo With Community Pool And Beach Access - Sea Club Ii Unit 2b

apartment, Siesta Key
This ground floor apartment is located on Siesta Key, just a short walk from the #1 ranked Siesta Key Beach and a mile from Siesta Village, offering a convenient location near shops, restaurants, and entertainment. The apartment has received excellent user ratings.
This one-bedroom, one-bathroom apartment is 520 square feet and comfortably accommodates four guests. Amenities include a fully equipped kitchen, a swimming pool, a spa, and a laundry facility, ensuring a comfortable and enjoyable stay.

Best Siesta Key, FL lodging with a balcony

Relaxing Siesta Key 3rd Floor Condo - Siesta Key, FL
9.7 101 reviews

Relaxing Siesta Key 3rd Floor Condo

apartment, Siesta Key
1 Bedroom 1 Bathroom Condominium With Partial South Gulf Views - Siesta Key, FL
9.6 119 reviews

1 Bedroom 1 Bathroom Condominium With Partial South Gulf Views

apartment, Siesta Key
Charming 2br Bayside Condo In Sarasota, Perfect For A Family Getaway. - Siesta Key, FL
9.2 41 reviews

Charming 2br Bayside Condo In Sarasota, Perfect For A Family Getaway.

apartment, Siesta Key
Salty Dog | Siesta Key Canal-front Escape! - Siesta Key, FL
No reviews

Salty Dog | Siesta Key Canal-front Escape!

apartment, Siesta Key

Best Siesta Key, FL lodging with a kitchen

Great Siesta Key Location! Short Walk To The Beach, Shopping & Dining And More! Vh302b - Siesta Key, FL
9.0 2 reviews

Great Siesta Key Location! Short Walk To The Beach, Shopping & Dining And More! Vh302b

apartment, Siesta Key
Siesta Key Retreat- 2/1 Condo W/pool, Beach Access - Siesta Key, FL
9.4 175 reviews

Siesta Key Retreat- 2/1 Condo W/pool, Beach Access

apartment, Siesta Key
Across The Street From Siesta Key Beach 314 - Siesta Key, FL
9.6 11 reviews

Across The Street From Siesta Key Beach 314

apartment, Siesta Key
Charming Chic Getaway - 2 Min. Walk To Beach, Restaurants, & Shops - Siesta Key, FL
10 24 reviews

Charming Chic Getaway - 2 Min. Walk To Beach, Restaurants, & Shops

apartment, Siesta Key

Best Siesta Key, FL lodging with laundry available

Skv 309 - Pool, Walk To Beach & Village! - Siesta Key, FL
10 2 reviews

Skv 309 - Pool, Walk To Beach & Village!

apartment, Siesta Key
Lj's Cottage 2 - Pool Beach Sunsets Balcony - Siesta Key, FL
10 12 reviews

Lj's Cottage 2 - Pool Beach Sunsets Balcony

apartment, Siesta Key
Steps To Siesta Key Beach 2 Bed 2 Bath With Full G - Siesta Key, FL
10 3 reviews

Steps To Siesta Key Beach 2 Bed 2 Bath With Full G

apartment, Siesta Key
This Third Floor 2 Bedroom 2 Bathroom Condominium Is Located On The Bayside - Siesta Key, FL
9.4 60 reviews

This Third Floor 2 Bedroom 2 Bathroom Condominium Is Located On The Bayside

apartment, Siesta Key
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