5754 Vacation rentals and Airbnb in Siesta Key, FL
Siesta Key, FL
04/07 – 08/07
₹31000/nighttotal: ₹124000 (4 )
91 M² Condo ∙ 2 Bedrooms ∙ 4 Guests
2 4
apartment , Siesta Key
This two-bedroom flat in Siesta Key is situated just 160 metres from the beach and conveniently close to dining and shopping near Stickney Point Bridge. This 91 square metre accommodation sleeps four guests and features a fully equipped kitchen, air conditioning, parking, an outdoor lanai, patio with a grill, and an outdoor shower.
9.6 14 reviews
Siesta Key, FL
22/06 – 27/06
₹38535/nighttotal: ₹192675 (5 )
Mid Century Siesta Key Escape 2br Villa W/ Pool & Dock
2 2
apartment , Siesta Key
This Siesta Key holiday home is located just 1.5 kilometres from Siesta Key Beach and Crescent Beach, offering a peaceful retreat close to the area's main attractions. The property has received excellent ratings for its cleanliness, location, and overall experience. The two-bedroom home spans 139 square metres and comfortably accommodates five guests. Enjoy a range of amenities, including a private pool, a garden, and access to a water park, ensuring a fun and relaxing stay.
9.7 29 reviews
Siesta Key, FL
19/06 – 21/06
₹95363/nighttotal: ₹190726 (2 )
Siesta Key Hideway -3 Bedroom Canal Pool Home
1 6
apartment , Siesta Key
This Siesta Key holiday home is peacefully situated on a tree-lined street, a short distance from Siesta Beach, Siesta Key Village, and Sarasota. The three-bedroom, three-bathroom property boasts a split-level design with an open-plan living area, a fully equipped kitchen including a dishwasher, a private heated pool (heating at an extra cost), and accommodates up to six guests, offering full access to the entire property.
9.5 156 reviews
Siesta Key, FL
10/07 – 12/07
₹40539/nighttotal: ₹81078 (2 )
Siesta Cooler: Only Minutes Walk To Siesta Beach!
1 2
apartment , Siesta Key
This apartment is located just 3 minutes' walk from Siesta Key Beach, one of the most beautiful beaches in the world, and is also within easy reach of Crescent Beach and The John and Mable Ringling Museum of Art. It has consistently received excellent ratings for location, cleanliness and overall guest experience. The flat has a spacious layout with a separate bedroom, living room and a fully equipped kitchenette, offering a comfortable and relaxing stay over its 74 square metres. It offers a range of amenities including a swimming pool, tennis court, garden, terrace and private parking, as well as free Wi-Fi, laundry facilities, and the option to rent a bicycle or car.
9.8 9 reviews
Siesta Key, FL
18/06 – 26/06
₹18392/nighttotal: ₹147136 (8 )
Sarasota Coastal Style - Minutes To Siesta Beaches - Casa De Suenos
2 4
apartment , Siesta Key
This Sarasota holiday home offers a spacious two-bedroom, two-bathroom apartment, ideally situated for exploring Siesta Key and Lido Key beaches, and St Armands Circle's shops and restaurants; distances to these attractions are not specified. The 97 square metre property features a well-equipped kitchen with stainless steel appliances, three smart TVs with Roku, a dedicated home office, and an expansive backyard; sleeping arrangements include queen-size pull-out sofas, accommodating up to six guests.
9.2 13 reviews
Siesta Key, FL
01/01 – 31/03
₹22871/nighttotal: ₹2035519 (89 )
Chic Peaceful 3bd Cottage - Walk To Siesta!
2 2
apartment , Siesta Key
Key Lime Surf Shack, a two-bedroom bungalow on Hollywood Boulevard in Siesta Key, Florida, is situated a 2.4km walk from Siesta Key Beach, consistently ranked among the top beaches in the USA. This self-catering property sleeps five guests and features a fully equipped kitchen with dishwasher, king and queen-size beds, a full-size washer/dryer, smart TVs with streaming access, and a shared spacious backyard.
9.3 140 reviews
Siesta Key, FL
19/06 – 21/06
₹49925/nighttotal: ₹99850 (2 )
Luxury Condo Steps From Siesta Key Beach & Village | Beach Gear | Smart Tvs & More!
1 6
apartment , Siesta Key
This Siesta Key apartment is located just 1.6 kilometres from Irma Beach and Siesta Key Beach, and 3.2 kilometres from Shell Beach, placing you in the heart of the bustling Siesta Key Village. It has excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment has two bedrooms and is 82 square metres in size. It offers a range of amenities including a swimming pool, parking, internet access, a kitchen with a fridge, microwave, and dishwasher, and air conditioning.
9.5 2 reviews
Siesta Key, FL
18/07 – 25/07
₹25778/nighttotal: ₹180446 (7 )
Firethorn 613 - 2 Bedroom Condo With Private Beach With Lounge Chairs & Umbrella Provided, 2 Pool...
2 2
apartment , Siesta Key
This Siesta Key waterfront apartment, situated in Midnight Cove, offers direct access to the pool, boat docks, and is a short walk from Crescent Beach. The 93-square-metre (over 1000 sq ft) property features two bedrooms, two bathrooms, a king-size bed, two twin beds, a sleeper sofa, and in-unit laundry facilities, accommodating up to six guests and providing access to nearby watersports.
9.8 8 reviews
Siesta Key, FL
25/07 – 30/07
₹35305/nighttotal: ₹176525 (5 )
Our House At The Beach C-120 Corner Townhouse Unit!
2 5
apartment , Siesta Key
This Siesta Key lake house, near Siesta Key Beach and Crescent Beach, offers convenient access to St. Armands Circle and the Mall at University Town Centre, though precise distances aren't specified. The 126 square metre (1356 square foot) two-bedroom, two-bathroom property boasts a spacious bi-level layout sleeping up to six guests, and includes a private pool, balconies, and a fully equipped kitchen with dishwasher and washer/dryer; nearby amenities include tennis courts and a BBQ pavilion.
9.6 62 reviews
Siesta Key, FL
27/06 – 07/07
₹25117/nighttotal: ₹251170 (10 )
Bayfront Balconies In Tropical Siesta Key With Sunrise Views & Walkable Beach Access
2 4
apartment , Siesta Key
This two-level condominium is situated in Siesta Key's downtown area, offering direct bay views for sunrises and opposite the beach for easy access, with Siesta Key Beach a 7-minute cycle and Crescent Beach a 10-minute walk away. This 111 square metre accommodation sleeps six across two bedrooms and two and a half bathrooms, featuring a modern kitchen with stainless steel appliances, a private laundry room, a balcony with pool views, and access to communal facilities including a tennis court, billiard room, sauna, and heated swimming pool, with complimentary daily access to select local attractions such as bike, kayak, or dolphin cruise rentals included.
10 1 review
Siesta Key, FL
16/07 – 19/07
₹26187/nighttotal: ₹78561 (3 )
1st Floor Condo In Lovely Siesta Key
1 2
apartment , Siesta Key
This first-floor condominium in Siesta Key provides direct bay access within the community and is a short 150-metre walk across the street to Crescent Beach and Siesta Key Cove, with a trolley stop directly outside for convenient access to Siesta Key Village and downtown Sarasota. This apartment, accommodating up to six guests, features a private patio with direct access to the communal swimming pool, a community dock on Siesta Key Bay for marine life viewing and fishing, and includes one dedicated parking space.
9.8 33 reviews
Siesta Key, FL
22/08 – 05/09
₹19094/nighttotal: ₹267316 (14 )
Harbor Tower Intracoastal Condo
3 3
house , Siesta Key
This Siesta Key property is located just a short walk from Crescent Beach and less than 1.6 km from Siesta Key Beach, offering easy access to the area's beautiful white sand beaches. The property has excellent user ratings for cleanliness, location and overall experience. The 163 square metre house provides comfortable accommodation for a family or group of friends. It boasts a fully equipped kitchen, a terrace, a garden, a swimming pool, a tennis court, and a range of other amenities, making it perfect for a relaxing and enjoyable stay.
Best family friendly Siesta Key, FL vacation rentals
Among the 5754 accommodations in Siesta Key, FL, here are the 4 best family friendly rentals
10 1 review
Siesta Key, FL
21/06 – 28/06
₹30586/nighttotal: ₹214102 (7 )
64 M² House ∙ 1 Bedroom ∙ 4 Guests
1 3
house , Siesta Key
This Aloha Kai #62 property is a 1-bedroom bungalow located on Siesta Key's Crescent Beach, offering direct access to the award-winning beach and close proximity to local eateries and bars, approximately 1.6 kilometres from the main shopping areas. This family-friendly accommodation, spanning 63 square meters and accommodating up to four guests, features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, spa, and parking, with community amenities including shuffleboard and ping pong, and complimentary beach toys available for use.
Siesta Key, FL
17/06 – 26/06
₹57721/nighttotal: ₹519489 (9 )
6415 Midnight Pass #311
3 6
house , Siesta Key
6415 Midnight Pass #311, a Siesta Key holiday home, is a short walk (7 minutes) from Crescent Beach and within 2.6 km of Turtle Beach and 2.9 km of Siesta Key Beach. This 223 square metre property boasts three bedrooms, two bathrooms, sleeps fifteen guests, and includes a private swimming pool, Jacuzzi, sauna, spa, fitness centre, tennis court, and parking; nearby attractions include The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport, both 18 km away.
10 1 review
Siesta Key, FL
18/07 – 25/07
₹17632/nighttotal: ₹123424 (7 )
70 M² Condo ∙ 1 Bedroom ∙ 4 Guests
1 2
apartment , Siesta Key
This Siesta Key condo, conveniently located near multiple beach access points and a 10-minute tram ride (approximately 1.6km) from Siesta Key Village, offers easy access to restaurants, bars, and shops. The 69 square metre (743 square feet) apartment features one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, screened lanai, king-size bed, Murphy bed, sleeper sofa, covered parking, elevator access, and access to a heated pool, tennis and pickleball courts, and a fishing pier.
9.8 15 reviews
Siesta Key, FL
21/10 – 25/10
₹33842/nighttotal: ₹135368 (4 )
Sunny Beach Retreat On Siesta Key
2 3
apartment , Siesta Key
This two-bedroom, two-bathroom condominium is located on Siesta Key, a short 100-metre walk from Siesta Key Beach, and close to the Breeze trolley stop for convenient access to local attractions. This 103 square metre apartment accommodates up to six guests and features a fully equipped kitchen, a private lanai overlooking a heated swimming pool, and complimentary beach supplies and fishing gear.
Best Siesta Key, FL vacation rentals with a pool
Among the 5754 accommodations in Siesta Key, FL, here are the 4 best rentals with a pool
9.7 96 reviews
Siesta Key, FL
13/07 – 17/07
₹19426/nighttotal: ₹77704 (4 )
New Luxury Unit Steps From The Ocean In Siesta Key
1 2
apartment , Siesta Key
This Siesta Key studio apartment is conveniently located near Crescent Beach, offering easy access to the sand. The newly remodelled self-catering unit sleeps two, boasts a full kitchen, private lanai, and is fully air-conditioned, perfect for a relaxing beach getaway.
9.5 112 reviews
Siesta Key, FL
23/12 – 28/12
₹29294/nighttotal: ₹146470 (5 )
Bay Oaks Ground Floor
2 2
house , Siesta Key
This holiday home is situated just a short walk from Crescent Beach and a little over a mile from Siesta Key Beach, offering a prime location for a relaxing beach getaway. The property has received excellent ratings for location, cleanliness, and overall user experience. This one-bedroom property is 80 square metres in size and offers comfortable accommodation for families or small groups. The home comes equipped with a fully fitted kitchen, air conditioning, a private swimming pool, a tennis court, and a garden, providing everything you need for a comfortable and enjoyable stay.
9.7 6 reviews
Siesta Key, FL
22/06 – 08/07
₹22451/nighttotal: ₹359216 (16 )
Harbor Towers – Bayfront Luxury With Pool & Tennis
1 6
apartment , Siesta Key
This 6th-floor corner condominium in Harbor Towers Yacht & Racquet Club, Siesta Key, offers panoramic sunrise-to-sunset views of the Gulf of Mexico and Sarasota Bay, located a mere 700-1000 metres walk from Siesta Beach and close to Siesta Key Village. This apartment sleeps six and boasts three bedrooms and two bathrooms, featuring a chef-inspired kitchen with a commercial-size stove, in-unit laundry, and access to resort-style amenities including a heated swimming pool, tennis and pickleball courts, and a waterfront grilling patio.
9.0 2 reviews
Siesta Key, FL
29/07 – 30/07
₹44261/nightfor 1 night
Modern Bright Escape Mins Beach, Pool, Hot Tub
1 5
apartment , Siesta Key
This Siesta Key apartment, an eight-minute walk from Crescent Beach, is 11.6km from Marina Jack and 17.7km from the Ringling Museum. The 70-square-metre self-catering flat offers one bedroom, one bathroom, sleeps ten guests, and includes a private pool, hot tub, free Wi-Fi, and parking.
Frequently asked questions about holiday rentals in Siesta Key, FL
What are some interesting places to visit in or near Siesta Key, FL?
Siesta Key is known for its beautiful beaches, but there's more to see. You can visit the Siesta Key Drum Circle, a vibrant gathering of musicians and dancers, or explore the historic Siesta Key Village with its shops and restaurants. For a day trip, head to nearby Sarasota, home to the Ringling Museum and the John and Mable Ringling Museum of Art.
What are the best Airbnb and vacation rentals in Siesta Key, FL?
Which walking or cycling routes are the best in Siesta Key, FL?
The Siesta Key Beach Walk is a popular choice for strolling along the shore, while the paved path along the Siesta Key Bridge offers scenic views of the water. For a more challenging ride, try the Legacy Trail, a 12-mile paved path connecting Sarasota to Venice, which is perfect for cycling.
What are the most popular Airbnbs in Siesta Key, FL?
What sports or outdoor activites can visitors enjoy in and around Siesta Key, FL?
Siesta Key is a haven for water sports enthusiasts, with plenty of opportunities for swimming, sunbathing, kayaking, paddleboarding, and jet skiing. You can also try your hand at fishing, or take a boat trip to see dolphins and manatees. For a more active experience, visit the Siesta Key Beach Park, which offers volleyball courts and a playground.
What are the best vacation rentals with a pool in Siesta Key, FL?
What other towns or cities can be easily accessed from Siesta Key, FL?
Sarasota is just a short drive from Siesta Key, offering a variety of cultural attractions and dining options. You can also easily reach the charming town of Venice, known for its beautiful beaches and historic downtown area. For a longer day trip, consider visiting St. Petersburg, a vibrant city with a bustling waterfront.
What are the best rentals for families and kids in Siesta Key, FL?
What amenities are commonly available in vacation rentals in Siesta Key, FL?
Vacation rentals in Siesta Key typically offer a range of amenities, including private pools, hot tubs, and outdoor grills. Many also feature fully equipped kitchens, laundry facilities, and comfortable living spaces. Some rentals even offer direct beach access or stunning ocean views.
What are the best rentals or Airbnbs with a jacuzzi in Siesta Key, FL?
What time of year is best to rent a vacation rental Siesta Key, FL?
Siesta Key is a popular destination year-round, but the best time to visit depends on your preferences. For warm weather and sunny skies, visit during the spring or autumn. If you prefer cooler temperatures and fewer crowds, consider visiting during the winter months. However, keep in mind that hurricane season runs from June to November.
What are the local dishes in Siesta Key, FL region?
The Siesta Key region is known for its fresh seafood. Try the local catch of the day, grilled or fried, or indulge in a delicious seafood platter. You can also find traditional Southern dishes like fried chicken, collard greens, and sweet tea. Don't forget to try the key lime pie, a local favourite.
Destinations nearby
Best Siesta Key, FL holiday rentals with a balcony
8.8 5 reviews
Siesta Key, FL
17/06 – 21/06
₹39102/nighttotal: ₹156408 (4 )
Our House At The Beach E-404 Sugar Sands Beach View!!
3 4
apartment , Siesta Key
This Siesta Key apartment is located just 1.6 kilometres from St. Boniface Episcopal Church Labyrinth and Siesta Key Beach, with Crescent Beach and Siesta Key Marina both within 3.2 kilometres, making it an ideal base for exploring this beautiful area. Guests have consistently rated this property as excellent, highlighting its comfortable and convenient features. The apartment offers two bedrooms and a sofa bed, providing ample space for up to four guests and covering 111 square metres. You'll enjoy a fully equipped kitchen, a private balcony, a swimming pool, a spa, and a garden, making it easy to relax and enjoy your Siesta Key holiday.
Siesta Key, FL
30/07 – 01/08
₹282671/nighttotal: ₹565342 (2 )
Island House Walk To Siesta Key Beach!
7 7
apartment , Siesta Key
This Siesta Key residence is located in Siesta Key Village, a 4-minute walk to Siesta Beach and within walking distance of local dining and shops. This spacious 7-bedroom, 6-bathroom holiday home accommodates up to 19 guests and features a private backyard with a heated pool, hot tub, and BBQ area, alongside a separate guest suite and ample parking for four vehicles.
Siesta Key, FL
26/06 – 27/06
₹368258/nightfor 1 night
Summer House | Walk To Beach & Siesta Key Village
6 2
apartment , Siesta Key
This ground-level holiday home is located in Siesta Key Village, just 180 metres from the renowned Siesta Key Beach and its surrounding shops and eateries. This spacious residence accommodates up to 20 guests with 6 bedrooms and 6 en-suite bathrooms, boasting a resort-style garden featuring a swimming pool with a grotto, waterslide, spa, outdoor bar, BBQ grill, and complimentary beach essentials.
9.3 9 reviews
Siesta Key, FL
30/07 – 01/08
₹26082/nighttotal: ₹52164 (2 )
* New * Serene Retreat / Private Patio & Pool *
2 3
apartment , Gulf Gate Estates
This Gulf Gate Estates apartment is situated a 19-minute walk from Crescent Beach and approximately 10.5km from both the Sarasota Opera House and Marina Jack, with other attractions within a 16km radius. The two-bedroom, two-bathroom flat sleeps six guests and boasts a private pool and patio, fully equipped kitchen, free Wi-Fi, private parking, and a washing machine; nearby activities include exploring Sarasota's attractions.
Best Siesta Key, FL holiday rentals with parking
8.6 235 reviews
Siesta Key, FL
17/06 – 21/06
₹32501/nighttotal: ₹130004 (4 )
Fanta-sea 55 By Beachside Management
1 4
house , Siesta Key
This beachfront property is located on Siesta Key, just a short walk from the famous Siesta Key Beach and a short drive from Crescent Beach, offering a peaceful retreat in a prime location. The property has received very good user ratings, with excellent scores for location and cleanliness. This four-bedroom house comfortably accommodates a larger group or family. Guests can enjoy a fully equipped kitchen, a private pool, a patio, a sun terrace, and barbecue facilities, as well as free parking and WiFi.
8.8 69 reviews
Siesta Key, FL
24/10 – 03/11
₹19381/nighttotal: ₹193810 (10 )
Beach Getaway Steps From The Sand W/ Shared Pool, Fast Wifi & Parking
1 2
apartment , Siesta Key
This Siesta Key Village flat is less than 3.2km from Siesta Key Beach and Irma Beach, and within 4.8km of Shell and Crescent Beaches, offering easy access to Siesta Key's renowned sands. The 29 square metre self-catering apartment sleeps two, and includes a kitchen with fridge and microwave, plus amenities such as free Wi-Fi, parking, a washing machine, and a swimming pool.
This Siesta Key apartment, located in La Siesta Condominiums, is steps from Siesta Key Beach and a short walk from Siesta Village. The 81-square-metre (870 sq ft) property boasts two bedrooms, one bathroom, and sleeps up to six guests, featuring a fully equipped kitchen, swimming pool access, and a screened lanai overlooking the pool.
10 21 reviews
Siesta Key, FL
26/06 – 27/06
₹93494/nightfor 1 night
Sea Escape - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach!
1 2
apartment , Siesta Key
This ground-floor flat in Siesta Key Village offers excellent walkability, located just 122 metres from Siesta Key Beach and a short walk to local shops and restaurants. This 50 square metre apartment accommodates up to four guests, featuring a private entrance, a kitchen with a fridge, microwave, and dishwasher, a patio with a grill, and shared amenities like chaise loungers, with free WiFi and parking provided.