Siesta Key, FL Short term rentals

5661 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Siesta Key, FL short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

Mallory Squared By Beachside Management - Siesta Key, FL
8.0 1 review

Mallory Squared By Beachside Management

apartment, Siesta Key
This Siesta Key rental, Mallory Squared, is a two-bedroom, two-bathroom apartment located a short walk from Crescent Beach and within 7-12 miles of Sarasota attractions like the Ringling Museum of Art and the Sarasota International Convention Center.
This 1300-square-foot condo sleeps up to 15 guests and features well-equipped kitchens, air conditioning, private entrances, and a desk and TV in each unit.

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.

Charming Bayfront 2 Brs Siesta Key Condo - Siesta Key, FL
9.7 87 reviews

Charming Bayfront 2 Brs Siesta Key Condo

apartment, Siesta Key
This bayfront condo rental is centrally located on Siesta Key, a 15-minute walk from Crescent Beach and a 5-minute drive from Siesta Key Beach and the Village.
The two-bedroom, one-bathroom unit sleeps four, features a full kitchen with dishwasher, offers a swimming pool and parking, and is close to Siesta Key Village's restaurants and shops.

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's Siesta | Palm-view Pools Private-beach! - Siesta Key, FL
9.9 19 reviews

Gertrude's Siesta | Palm-view Pools Private-beach!

apartment, Siesta Key
This 2-bedroom, 2-bathroom condo on Siesta Key's bay side offers a top-floor unit with direct bay-front and private beach access, a 4-minute walk to Siesta Beach and immediate proximity to free trolleys for shopping and dining. Enjoy resort-style amenities including heated pools, a jacuzzi, fitness center, and tennis/pickleball courts, along with a 40-foot balcony perfect for sunset views, accommodating up to 6 guests.
Newly Renovated 1 Bedroom Condo - Siesta Key, FL
No reviews

Newly Renovated 1 Bedroom Condo

apartment, Siesta Key
This 1-bedroom condo in Siesta Key is located a short distance from St. Armands Circle and the Mall at University Town Center, and is close to Siesta Key Beach and Crescent Beach.
This family-friendly rental accommodates up to 4 guests and offers a swimming pool, air conditioning, internet, and a kitchen equipped with a fridge, microwave, and dishwasher.
Gertrude's Siesta | Bayview Unit, Near Beach, Private Patio, Heated Pool, Pickle,tennis! - Siesta Key, FL
10 3 reviews

Gertrude's Siesta | Bayview Unit, Near Beach, Private Patio, Heated Pool, Pickle,tennis!

apartment, Siesta Key
This ground-floor, single-level Siesta Key apartment offers a private patio with bay views and is a 1-minute walk to the bay and pool, a 15-minute walk to Siesta Beach access 12, and a 2-minute walk to the free Siesta Trolley.
This family-friendly 690 sq ft condo accommodates up to 6 guests with 3 bedrooms and 1 bathroom, featuring a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, garden, parking, and resort amenities including tennis/pickleball courts and a fishing dock.
120 M² Condo ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
10 3 reviews

120 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Siesta Key
This South Siesta Key condo is located 0.3 miles from Siesta Key's famed white-sand beaches, and less than 0.2 miles from restaurants like Captain Curt's and The Daiquiri Deck, plus the Siesta Key Marina.
This 1280-square-foot vacation rental boasts two bedrooms (king and two queen beds), two bathrooms, a sleeper sofa, private balcony, and access to a shared pool, fitness center, tennis court, and spa, accommodating up to six guests.

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.

Charming 2-bedroom Bayside T Model Condo In Sarasota With Courtyard Views. - Siesta Key, FL
9.8 30 reviews

Charming 2-bedroom Bayside T Model Condo In Sarasota With Courtyard Views.

apartment, Siesta Key
This first-floor condo on Siesta Key's Bay side offers easy access to white sandy beaches, including Siesta Key Beach and Crescent Beach, and is a short drive to St. Armands Circle and the Mall at University Town Center.
This 1090 sq ft residence accommodates up to 6 guests, featuring 2 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, Jacuzzi, garden, and parking.

Best Siesta Key, FL lodging with a balcony

Romantic Getaway Beach Club Siesta 202b By Rva - Siesta Key, FL
8.9 64 reviews

Romantic Getaway Beach Club Siesta 202b By Rva

apartment, Siesta Key
Three Bedroom Condo At Midnight Cove Ii - Siesta Key, FL
9.1 132 reviews

Three Bedroom Condo At Midnight Cove Ii

apartment, Siesta Key
Salt & Sol - Your Siesta Key Retreat For 6 - Siesta Key, FL
No reviews

Salt & Sol - Your Siesta Key Retreat For 6

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

110 M² Condo ∙ 2 Bedrooms ∙ 5 Guests

apartment, Siesta Key

Best Siesta Key, FL lodging with a kitchen

Beechwood Suites D - Siesta Key, FL
9.9 87 reviews

Beechwood Suites D

apartment, Siesta Key
Luxury Condo Ground Floor Across The Street From The #1 Beach - Siesta Key, FL
9.2 95 reviews

Luxury Condo Ground Floor Across The Street From The #1 Beach

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
Siesta Key Condo.  Checkout Our Great Rates! - Siesta Key, FL
9.9 140 reviews

Siesta Key Condo. Checkout Our Great Rates!

apartment, Siesta Key

Best Siesta Key, FL lodging with laundry available

Bougie Beach Bungalow  Siesta Key, Florida - Siesta Key, FL
10 20 reviews

Bougie Beach Bungalow Siesta Key, Florida

apartment, Siesta Key
Sea Breeze - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach! - Siesta Key, FL
10 46 reviews

Sea Breeze - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach!

apartment, Siesta Key
E62 - Amazing Siesta Key Condo On The Water! - Siesta Key, FL
9.4 13 reviews

E62 - Amazing Siesta Key Condo On The Water!

apartment, Siesta Key
Unwind In Style At Bay Oaks E-93: Tennis Court And Shared Pool Near Beach - Siesta Key, FL
9.4 3 reviews

Unwind In Style At Bay Oaks E-93: Tennis Court And Shared Pool Near Beach

apartment, Siesta Key
©2026 cozycozy.com