Best Short term and Weekly rentals in Siesta Key, FL
9.8 102 reviews
Siesta Key, FL
07/17 – 07/24
$615/nighttotal: $4305 (7 )
Spacious ~ Private Beach~shuffleboard~pool
2 8
apartment , Siesta Key
This Siesta Key vacation home is ideally situated less than a mile from Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offering easy access to pristine beaches and water activities. The two-bedroom house, sleeping up to six guests, boasts a fully equipped kitchen, private pool, Jacuzzi, and free Wi-Fi; nearby attractions include the Siesta Key Beach Playground and St. Boniface Episcopal Church Labyrinth.
9.6 71 reviews
Siesta Key, FL
10/03 – 10/31
$145/nighttotal: $4060 (28 )
Pineapple Cove: Ground-floor Comfort; Short Walk To Beach, Dining & Shops!
1 2
apartment , Siesta Key
This one-bedroom apartment is located just a short walk from both Crescent Beach and Siesta Key Beach, offering easy access to the area's famous white sand shores. It has received excellent ratings for location, cleanliness, and overall user experience. The 690 square foot apartment can comfortably accommodate up to 4 guests and features a fully equipped kitchen, a washing machine, a sofa bed, and a Smart TV with a DVD player. Enjoy amenities like air conditioning, a garden, parking, and internet access for a comfortable and enjoyable stay.
9.8 34 reviews
Siesta Key, FL
07/09 – 07/11
$1993/nighttotal: $3986 (2 )
Endless Views | Walking Distance To Siesta Key Beach + Village W/ Rooftop Panoramic Views!
3 4
apartment , Siesta Key
This beachfront vacation home sits less than 1.2 miles from Siesta Key Beach and St. Boniface Episcopal Church Labyrinth, with Irma and Shell Beaches within 3 miles. This 2,630-square-foot house features three bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, private balcony, barbecue grills, and free internet.
10 5 reviews
Siesta Key, FL
07/04 – 07/08
$313/nighttotal: $1252 (4 )
Charming Condo Ideally Located Near Crescent Beach On Famous Siesta Key️
1 4
apartment , Siesta Key
This Siesta Key condo, a three-minute walk from Crescent Beach, offers convenient access to local grocery stores and restaurants. The one-bedroom apartment sleeps four, features a fully equipped kitchen, BBQ grill, and includes beach chairs, umbrella, and cooler for guest use.
Siesta Key, FL
06/22 – 07/08
$188/nighttotal: $3008 (16 )
Beachside Bliss Walk To Siesta Pool Access
1 6
apartment , Siesta Key
This Sarasota condo offers a prime location in Siesta Key, just a 9-minute walk to Crescent Beach and approximately 7.2 miles from Marina Jack and Sarasota Opera. This 1050 sq ft condo accommodates up to 7 guests with two bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, free WiFi, and on-site parking.
9.9 66 reviews
Siesta Key, FL
08/09 – 08/15
$233/nighttotal: $1398 (6 )
Beach Rd, 300ft To Beach Access & 500ft To Village
1 2
apartment , Siesta Key
This Siesta Key studio apartment is located just 328 feet from Siesta Key Beach and under a 5-minute walk from Siesta Village, offering easy access to shops and restaurants. The open-plan unit features a queen-sized bed, kitchenette with fridge, freezer, and microwave, and accommodates two guests; free amenities include high-speed Wi-Fi, beach essentials, and reserved parking.
9.7 53 reviews
Siesta Key, FL
09/06 – 09/13
$168/nighttotal: $1176 (7 )
2bed 2 Bath Entire Condo Beach Getaway
1 2
apartment , Siesta Key
This Siesta Key condo is located just a short 3-block walk from the world-famous Siesta Key Beach, offering easy access to the area's top attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall experience. This 2-bedroom, 2-bathroom unit can comfortably accommodate up to 4 guests. Enjoy lagoon views from the screened-in balcony, a modern kitchen, and access to a pool, fitness center, and tennis courts.
9.9 90 reviews
Siesta Key, FL
07/10 – 07/12
$282/nighttotal: $564 (2 )
Bayside Bliss Siesta Key, Beach Access, Boat Slip
1 2
apartment , Siesta Key
This Siesta Key condo boasts a prime location between the beach and the bay, a short 1.5-mile trolley ride from Siesta Key Village and offering private deeded beach access within a 5-minute walk. This one-bedroom, one-bathroom unit sleeps four, features a heated pool, tiki bar, fishing pier, and a boat slip accommodating boats up to 24 feet, plus a kitchen with a fridge, freezer, and microwave.
Siesta Key, FL
06/27 – 07/07
$196/nighttotal: $1960 (10 )
The Terra Grove Villa - Sk Collection
1 4
apartment , Siesta Key
This Terra Grove Villa in Siesta Key offers convenient access to attractions such as Marina Jack Restaurant and Marina (7.4 miles) and Sarasota Opera (7.5 miles). This 1210 sq ft apartment accommodates up to 7 guests with 2 bathrooms, featuring air conditioning, a private pool, a fully equipped kitchen, a terrace, and complimentary high-speed Wi-Fi and parking.
9.7 96 reviews
Siesta Key, FL
07/13 – 07/17
$206/nighttotal: $824 (4 )
New Luxury Unit Steps From The Ocean In Siesta Key
1 2
apartment , Siesta Key
This newly remodeled Siesta Key studio is located steps from Crescent Beach, offering easy beach access ideal for travelers with mobility concerns. The 1-bedroom unit, sleeping up to 2 guests, features a full kitchen, private lanai, and a full bathroom; nearby amenities include a swimming pool and parking.
9.6 63 reviews
Siesta Key, FL
06/19 – 06/21
$301/nighttotal: $602 (2 )
Siesta Shores 2bed/2bath Heated Pool!
2 4
apartment , Siesta Key
This Siesta Key apartment rental is a 10-minute walk from Siesta Key Beach, restaurants, bars, and the marina. The newly renovated two-bedroom, two-bathroom unit sleeps six and includes a fully equipped kitchen, in-unit laundry, complimentary Wi-Fi, parking, and pool access; beach chairs and linens are provided.
9.6 30 reviews
Siesta Key, FL
09/03 – 09/11
$272/nighttotal: $2176 (8 )
Condo# 319 Located Across The Street From Siesta Key Beach, Gulf And Pool View Condo!!
2 3
apartment , Siesta Key
This 2-bedroom, 1-bathroom condo is located in La Siesta Condominiums, directly across the street from Siesta Key Beach and a short walk from Siesta Village. The 870-square-foot apartment features a private balcony, a fully equipped kitchen, and a swimming pool, accommodating up to six guests.
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.
9.4 325 reviews
Siesta Key, FL
07/06 – 07/13
$419/nighttotal: $2933 (7 )
Walk To Siesta Key Beach & Village | Private Patio | Prime Location!
1 2
apartment , Siesta Key
This family-friendly apartment is located just two miles from Siesta Key Beach and Irma Beach, offering easy access to the area's beautiful shores. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience. This one-bedroom, one-bathroom unit comfortably accommodates two guests. The apartment offers a fully equipped kitchen, a private laundry, free Wi-Fi, a TV, and access to a swimming pool, garden, and parking.
9.3 9 reviews
Siesta Key, FL
07/09 – 07/11
$290/nighttotal: $580 (2 )
* New * Serene Retreat / Private Patio & Pool *
2 4
apartment , Gulf Gate Estates
This Gulf Gate Estates rental is conveniently located near Crescent Beach, a 19-minute walk away, and within a 6.5-mile radius of the Sarasota Opera and Marina Jack. This two-bedroom, two-bathroom condo sleeps six guests and boasts a private pool and patio, free Wi-Fi, free parking, a fully equipped kitchen with dishwasher, and a washer/dryer.
9.2 342 reviews
Siesta Key, FL
07/12 – 07/14
$309/nighttotal: $618 (2 )
Siesta Palms By The Beach
1 2
aparthotel , Siesta Key
Siesta Palms By the Beach is located in Sarasota, Florida, just minutes from Crescent Beach and Turtle Beach, and within a short drive of the John and Mable Ringling Museum of Art and the Sarasota Opera. This aparthotel has excellent user, location, and cleanliness ratings. The aparthotel offers spacious accommodations with fully equipped kitchens, private balconies, and modern amenities. Guests can enjoy a range of on-site amenities, including a swimming pool, hot tub, and garden, as well as convenient access to the beach.
9.9 35 reviews
Siesta Key, FL
08/01 – 08/09
$304/nighttotal: $2432 (8 )
Sweet Siesta Cottage
1 2
apartment , Siesta Key
This Siesta Key vacation home is located directly across from Siesta Key Beach, steps from the village's shops and restaurants, and a short walk from the Sunday Farmers Market. The two-bedroom, one-bathroom cottage sleeps four, features a full kitchen, air conditioning, Wi-Fi, pet-friendly accommodations, on-site parking, and boasts vintage surf decor.
Best Siesta Key, FL lodging with a balcony
9.2 120 reviews
Siesta Key, FL
08/01 – 08/09
$619/nighttotal: $4952 (8 )
Steps To Beach. Shared Pool Pet/family Friendly. Parking Incl.
3 2
apartment , Siesta Key
This Siesta Key vacation home is located within a mile of Siesta Key Beach and St. Boniface Episcopal Church Labyrinth, and within three miles of Irma Beach and Crescent Beach, making it a convenient base for exploring the area. Guests have consistently rated the home excellent for location, cleanliness, and overall experience. This 3-bedroom, 1800 square foot vacation home provides a comfortable and spacious layout for families or groups of friends. Enjoy features like a private pool, spa, tennis court, and a fully equipped kitchen, as well as amenities like air conditioning, internet, and a washing machine.
9.5 20 reviews
Siesta Key, FL
06/20 – 06/27
$410/nighttotal: $2870 (7 )
Paradise Awaits!
2 6
apartment , Siesta Key
This Siesta Key condo rental is conveniently located less than a mile from Crescent Beach and Siesta Key Beach, and within a 10-minute drive of Siesta Key Marina and Point of Rocks. This two-bedroom, two-bathroom vacation rental sleeps six guests and boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, a private terrace, and access to a community pool, jacuzzi, and BBQ grills.
Siesta Key, FL
08/09 – 08/15
$239/nighttotal: $1434 (6 )
506 Siesta
2 2
apartment , Siesta Key
This 2-bedroom maisonette in Siesta Key is located within a complex, 250 meters from Siesta Key Beach and 10 meters from swimming waters, with the town center and grocery store a short walk away. This 1100 sq ft residence accommodates up to 6 guests and features a fully equipped kitchen, a balcony, air conditioning, WiFi, on-site parking, and access to a communal pool and racquet facilities.
9.8 19 reviews
Siesta Key, FL
07/09 – 07/11
$552/nighttotal: $1104 (2 )
Beachside Villa In Siesta Key | Canal Front | Pool
1 4
apartment , Siesta Key
This Siesta Key Village rental is less than a mile from Siesta Key Beach and two miles from the Siesta Key Farmers Market, offering convenient access to local attractions. The two-bedroom, one-bathroom house sleeps four and includes a fully equipped kitchen with fridge and microwave, in-unit laundry, a balcony, and gas grills for outdoor cooking.
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?
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.
Destinations nearby
Best Siesta Key, FL lodging with a kitchen
9.6 26 reviews
Siesta Key, FL
08/22 – 09/05
$138/nighttotal: $1932 (14 )
"The Boho Beach Hut" (Entire Condo)
1 3
apartment , Siesta Key
This Siesta Key condo, an eight-minute walk from Siesta Key Beach and near Siesta Key Village (accessible by the free trolley), offers convenient access to the beach, restaurants, and the Siesta Key public restrooms and children's park. The two-bedroom, two-bathroom unit sleeps six, features a king and queen bed, in-unit laundry, a screened porch, and includes beach chairs, towels, and a cooler for guest use, along with a Pack 'n Play for infants.
9.5 76 reviews
Siesta Key, FL
06/17 – 06/26
$229/nighttotal: $2061 (9 )
Vista Hermosa Cabana - Enjoy The Beach Life Here On The Island!!!!
2 6
apartment , Siesta Key
This Siesta Key apartment is conveniently located within a mile of Crescent Beach and Siesta Key Beach, and just two miles from Turtle Beach, offering easy access to the island's most popular stretches of white sand. It boasts consistently excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay. The apartment is spacious, offering 1400 square feet and comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a washing machine, two bathrooms, internet access, and a designated smoking area, ensuring a convenient and enjoyable stay.
10 10 reviews
Siesta Key, FL
07/25 – 07/30
$381/nighttotal: $1905 (5 )
Siesta Key Summer | 2br Walk To Beach + Pool
2 5
apartment , Siesta Key
This Siesta Key condo rental is conveniently located near Crescent Beach and Siesta Key Beach, a 15-minute walk away, and 2.1 miles from Turtle Beach. This 1300-square-foot apartment features three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, jacuzzi, tennis court, and free Wi-Fi.
9.6 264 reviews
Siesta Key, FL
07/09 – 07/11
$850/nighttotal: $1700 (2 )
Star Fish. 3 Bed 2 Bath. Pool. Daily Rentals
1 4
apartment , Siesta Key
This waterfront vacation rental is located just a short walk from Siesta Key Marina and Crescent Beach, with Siesta Key Beach and Turtle Beach within a 3-mile radius. It has consistently received excellent ratings for location, cleanliness, and overall experience. This comfortable home has 3 bedrooms and 2 bathrooms, accommodating up to 6 guests. Amenities include a fully equipped kitchen, laundry facilities, a private pool, a patio, and BBQ grills, ensuring a relaxing and enjoyable stay.
Neighborhoods and points of interest in Siesta Key, FL
Best Siesta Key, FL lodging with laundry available
9.6 254 reviews
Siesta Key, FL
06/24 – 06/29
$487/nighttotal: $2435 (5 )
Bh · 2/2 Beach House Apt On Siesta Key
2 2
apartment , Siesta Key
This Siesta Key apartment is located just a 15-minute walk from the world-famous Siesta Key Beach and Crescent Beach, and within a mile of the Siesta Key Marina and St. Boniface Episcopal Church Labyrinth. Guests consistently rate the apartment excellent for its location, cleanliness, and overall experience. This home features a fully equipped kitchen, in-unit laundry, and a comfortable living space perfect for families or groups of up to 6 guests. Enjoy amenities like a swimming pool, garden, and bar, along with internet access and parking.
9.5 156 reviews
Siesta Key, FL
07/10 – 07/12
$425/nighttotal: $850 (2 )
Siesta Cooler: Only Minutes Walk To Siesta Beach!
1 2
apartment , Siesta Key
This Siesta Key apartment is just a short walk from the famous Siesta Key Beach, making it ideal for enjoying the sun, sand, and water. Guests consistently rate the location, cleanliness, and overall experience as excellent. This one-bedroom unit offers 800 square feet of comfortable living space. Enjoy amenities like a private balcony, a well-equipped kitchen, a swimming pool, a tennis court, and free Wi-Fi.
10 1 review
Siesta Key, FL
07/02 – 07/06
$315/nighttotal: $1260 (4 )
70 M² Condo ∙ 1 Bedroom ∙ 4 Guests
1 2
apartment , Siesta Key
This Siesta Key condo offers a prime location near Sarasota, with easy trolley access to multiple beach access points and a short tram ride to Siesta Key Village's shops and restaurants. The 740-square-foot unit features one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, screened lanai, covered parking, and access to a heated pool, tennis/pickleball court, and fishing pier.
9.8 226 reviews
Siesta Key, FL
07/06 – 07/10
$286/nighttotal: $1144 (4 )
Steps To Beach & Siesta Key Village-village Condo
1 3
apartment , Siesta Key
This ground-level apartment is in Siesta Key Village, just steps from the beach and within walking distance of restaurants, shops, and the Siesta Key Market. The apartment has excellent user, location, and cleanliness ratings. The apartment has two bedrooms and one bathroom, accommodating up to four guests. It features a private patio, a fully equipped kitchen, and an outdoor shed for beach equipment.
