Best Holiday rentals and Airbnb offers in Siesta Key, FL
9.3 75 reviews
Siesta Key, FL
09/07 – 11/07
SG$695/nighttotal: SG$1390 (2 )
Beach Club | Heated Pool Near Beach | Modern Condo | Gated Access To Beach | Sleeps 6
2 4
apartment , Siesta Key
This Siesta Key oceanfront apartment, near Crescent Beach, is less than 1.5km from Siesta Key Beach and a 15-minute walk from Siesta Key Marina. The 71 square metre property boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, private terrace, swimming pool, Jacuzzi, and free parking.
9.2 159 reviews
Siesta Key, FL
25/12 – 02/01
SG$627/nighttotal: SG$5016 (8 )
Premium 2bd Condo Close To The Beach (An802)
2 5
apartment , Siesta Key
This Siesta Key apartment is ideally located just a short walk from Siesta Key Marina and Crescent Beach, offering easy access to the area's best attractions. Guests consistently rate the apartment highly for its excellent location, cleanliness, and overall experience. The apartment features a comfortable layout with two bathrooms, a balcony, and a TV. It also provides a range of amenities, including a kitchen with a fridge, microwave, and dishwasher, a swimming pool, a jacuzzi, a fitness centre, and a tennis court, ensuring a relaxing and enjoyable stay.
10 2 reviews
Siesta Key, FL
04/07 – 11/07
SG$307/nighttotal: SG$2149 (7 )
Private Beach Access Condo At Siesta Bayside
2 4
house , Siesta Key
This Key West-style holiday flat is situated in the Gulf & Bay Club Bayside gated community on Siesta Key, offering private beach access directly across the street to Siesta Key Beach and a 1.2 to 1.6 kilometre walk to dining and shopping. This two-bedroom, one-bathroom apartment accommodates up to four guests and features a newly renovated kitchen, air conditioning, a swimming pool, garden, parking, and access to the community's amenities including tennis courts, a fitness room, and a dock for dolphin watching, with beach equipment provided.
Siesta Key, FL
04/09 – 08/09
SG$466/nighttotal: SG$1864 (4 )
Siesta Beach House #304
1 8
apartment , Siesta Key
Siesta Beach House #304 is a detached house situated in Siesta Key, an 8-minute walk from Crescent Beach and approximately 17.7 kilometres from the John and Mable Ringling Museum of Art. This property offers 92 square metres of living space, accommodating up to 15 guests with 2 bathrooms, a fully equipped kitchen including a dishwasher and oven, air conditioning, and a private swimming pool with an outdoor seating area.
10 5 reviews
Siesta Key, FL
25/06 – 01/07
SG$333/nighttotal: SG$1998 (6 )
Siesta Key Condo - Short Walk To Beach - Gbb 1219
2 4
apartment , Siesta Key
This Siesta Key apartment is a ground-floor unit, a short walk (less than 0.8 km) from Siesta Key's renowned number one beach, directly opposite the community pool and tennis/pickleball courts. The two-bedroom, two-bathroom property sleeps four, boasts a fully equipped kitchen, two-car garage, access to a fitness centre, and includes provided linens and beach equipment; enjoy the on-site fishing dock and beautifully landscaped grounds.
9.8 25 reviews
Siesta Key, FL
14/07 – 11/08
SG$232/nighttotal: SG$6496 (28 )
White Sands Walk To Siesta Beach
2 3
house , Siesta Key
This Siesta Key property is a short walk from two of the area's most popular beaches, Crescent Beach and Siesta Key Beach, offering easy access to the sand and surf. The accommodation has received excellent ratings for location, cleanliness, and overall experience. The house itself is a comfortable 100 square metres in size. It comes equipped with a range of amenities including a fully equipped kitchen, air conditioning, free Wi-Fi, and a private parking space.
9.8 272 reviews
Siesta Key, FL
02/07 – 05/07
SG$515/nighttotal: SG$1545 (3 )
Near Beach. Daily Rentals. Pool. King Bed
1 2
apartment , Siesta Key
This ground floor apartment is located on Siesta Key, just 0.8 kilometres from Crescent Beach, a popular spot for swimming and sunbathing. It has excellent ratings for location, cleanliness, and user experience. The apartment has one bedroom and one bathroom, making it ideal for couples or solo travellers. It offers a range of amenities, including a private entrance, a heated swimming pool, a private beach, and free parking.
9.8 7 reviews
Siesta Key, FL
14/08 – 21/08
SG$548/nighttotal: SG$3836 (7 )
Lj's Cottages 1 - Pool Beach Sunset
2 8
apartment , Siesta Key
This Siesta Key apartment is situated less than 1.6km from Crescent Beach and Siesta Key Beach, and around 3.2km from Turtle Beach, offering easy access to Siesta Key's renowned sands. The three-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and parking; nearby barbecue grills are available for outdoor use.
10 114 reviews
Siesta Key, FL
04/08 – 05/08
SG$851/nightfor 1 night
Your Dreamoasisawaits: Siestakeyescape With Pool!
1 4
apartment , Siesta Key
This Siesta Key holiday home is situated 1.6km from Siesta Key's beaches, offering easy access to the island's attractions. The two-bedroom, two-bathroom property sleeps six, boasting a private pool, fully equipped kitchen, and open-plan living space with a king-size, queen-size bed and queen-size sofa bed.
9.4 37 reviews
Siesta Key, FL
05/07 – 11/07
SG$1249/nighttotal: SG$7494 (6 )
Casa Coquina | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps To Beach!
4 12
apartment , Siesta Key
This Siesta Key beachfront property is situated within 2km of Crescent Beach and Siesta Key Beach, and a 15-minute drive from Point of Rocks and Siesta Key Marina. This 186 square metre house boasts four bedrooms, three bathrooms, sleeps fourteen guests, and includes a private pool, tennis court, games room, and gas grills.
9.3 46 reviews
Siesta Key, FL
26/07 – 08/08
SG$328/nighttotal: SG$4264 (13 )
Awesome 2bd Condo Near The Beach (An799)
2 3
apartment , Siesta Key
This apartment is located just a short walk from Crescent Beach and less than 1.6km from Siesta Key Beach, offering easy access to the area's beautiful beaches and vibrant atmosphere. The property has received excellent ratings for location, cleanliness and overall user experience. The two-bedroom apartment comfortably accommodates six guests and features a balcony, two bathrooms, and a fully equipped kitchen. Guests can enjoy amenities such as a swimming pool, tennis court, fitness centre, sauna and spa, as well as free parking and internet access.
9.6 32 reviews
Siesta Key, FL
04/07 – 08/07
SG$546/nighttotal: SG$2184 (4 )
Best Value 1br Walk To Beach, Dining & Nightlife!
1 4
apartment , Siesta Key
This Siesta Key beachfront flat is less than 1.6km from Crescent Beach and Siesta Key Beach, and roughly 3.2km from Turtle Beach, offering easy access to three of the island's most popular stretches of sand. The self-catering apartment sleeps four, boasting a fully equipped kitchen, private balcony, free Wi-Fi, and on-site parking; a washing machine is also available for longer stays.
Best family friendly Siesta Key, FL holiday rentals
Among the 5754 accommodations in Siesta Key, FL, here are the 4 best family friendly rentals
9.8 18 reviews
Siesta Key, FL
01/08 – 06/08
SG$474/nighttotal: SG$2370 (5 )
Best Value 2br Walk To Beach, Dining & Nightlife
2 5
apartment , Siesta Key
This Siesta Key beachfront apartment is less than 1.6km from Crescent Beach and Siesta Key Beach, and around 3.2km from Turtle Beach. Sleeping up to eight guests, this two-bedroom flat boasts a private balcony, free Wi-Fi, on-site parking, and a kitchen equipped with a fridge and microwave.
10 1 review
Siesta Key, FL
06/07 – 13/07
SG$256/nighttotal: SG$1792 (7 )
97 M² House ∙ 2 Bedrooms ∙ 6 Guests
2 3
house , Siesta Key
This Sarasota dwelling is located close to Siesta Key and Lido Key beaches, offering convenient access to coastal attractions within 5 kilometres. This family-friendly property spans 96 square metres and accommodates up to six guests, featuring two bedrooms, two bathrooms, a well-equipped kitchen, a dedicated workspace, and an expansive backyard with Smart TVs and provided beach chairs.
10 1 review
Siesta Key, FL
06/07 – 13/07
SG$333/nighttotal: SG$2331 (7 )
112 M² Condo ∙ 2 Bedrooms ∙ 4 Guests
2 4
apartment , Siesta Key
This two-bedroom flat in the Gulf & Bay Club Bayside community offers direct intercoastal waterway frontage, providing views of marine life and is a short 500-meter walk from Siesta Key Village and the beach. This 111-square-meter apartment accommodates up to four guests and features resort-style amenities including two heated swimming pools, tennis and pickleball courts, a fitness centre, and secure garage parking.
9.7 113 reviews
Siesta Key, FL
08/07 – 10/07
SG$807/nighttotal: SG$1614 (2 )
Newly Renovated Condo Steps From Sk Private Beach
1 4
apartment , Siesta Key
This Siesta Key townhouse, a minute's walk (less than 0.2 km) from the private beach access on Siesta Key Beach and a short trolley ride from Siesta Key Village, offers convenient access to both the beach and local amenities. The two-storey property sleeps six guests, boasting two bedrooms (one king, one with two double beds), two bathrooms, a fully equipped eat-in kitchen, and provides beach toys, a wagon, and cooler for guest use.
Best Siesta Key, FL holiday rentals with a pool
Among the 5754 accommodations in Siesta Key, FL, here are the 4 best rentals with a pool
9.9 151 reviews
Siesta Key, FL
01/07 – 03/07
SG$456/nighttotal: SG$912 (2 )
Your Modern Beachside Getaway!
1 3
apartment , Siesta Key
This Siesta Key beachfront flat is a three-minute walk from Siesta Key Beach and directly opposite numerous restaurants and shops. The newly remodelled one-bedroom apartment sleeps four, boasting a modern kitchen, hotel-quality bed, and access to a communal pool, patio, courtyard, and barbecue area; on-site parking is also provided.
9.0 4 reviews
Siesta Key, FL
04/07 – 09/07
SG$447/nighttotal: SG$2235 (5 )
Anchorage Resort 2 Bedroom Condo With Beach Access
1 3
apartment , Siesta Key
This Anchorage Resort condo offers private beach access to Crescent Beach on Southern Siesta Key, with the Siesta Key Trolley stopping directly outside for convenient travel to Siesta Key Village. This two-bedroom, two-bathroom apartment accommodates up to six guests and boasts a fully equipped kitchen, a spacious balcony with canal views, and access to the resort's extensive amenities including the largest community pool on the Key and tennis courts, alongside complimentary beach supplies.
10 2 reviews
Siesta Key, FL
04/08 – 05/08
SG$4318/nightfor 1 night
Seashell Esta Luxe Siesta Key Escape
7 4
apartment , Siesta Key
This luxury Siesta Key holiday home is situated in Siesta Key Village, a 2-minute walk from Siesta Key Beach and close to local dining and shopping establishments. Boasting 7 bedrooms and 8 bathrooms, this expansive property accommodates up to 20 guests and features a resort-style backyard with a heated lagoon-style pool, spa, waterslide, a rooftop deck with Gulf views, elevator access to all three levels, and is equipped with beach essentials.
10 11 reviews
Siesta Key, FL
27/06 – 04/07
SG$285/nighttotal: SG$1995 (7 )
111 M² Condo ∙ 2 Bedrooms ∙ 4 Guests
2 2
apartment , Siesta Key
This apartment is located on Siesta Key's bay side, south of Sarasota, offering private access to Siesta Key Beach and a 5-10 minute walk to Siesta Village's shops and restaurants. This 111 square meter condominium sleeps four guests in two bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, fitness centre, and a terrace, with beach chairs and toys provided for your use.
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 are also some great places to visit nearby. You can head to the nearby city of Sarasota to visit the Ringling Museum of Art and the John and Mable Ringling Museum of Art, or check out the Mote Marine Laboratory & Aquarium.
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 paved Siesta Key Beach Walk is a great option for a stroll along the beach. If you're looking for a longer walk, the Legacy Trail is a 12-mile paved trail that connects to the Sarasota County area. For cycling, the paved Siesta Key Beach Access Road is a popular choice.
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 popular destination for swimming, sunbathing, and kayaking. If you're looking for something more adventurous, you can go parasailing, jet skiing, or even try stand-up paddleboarding. There are also several golf courses and tennis courts in the area.
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?
Siesta Key is located just south of Sarasota, which is a great city to visit. Sarasota has a vibrant downtown area with plenty of shops, restaurants, and cultural attractions. You can also easily reach the city of Venice to the south, which is known for its beautiful beaches and historic downtown.
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 grilling areas. Many rentals also have fully equipped kitchens, laundry facilities, and high-speed internet access.
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?
The best time to visit Siesta Key is during the spring or autumn months, when the weather is pleasant and the crowds are smaller. Summer can be hot and humid, and the winter months can be cool and rainy. You'll find the most affordable rates during the off-season.
What are the local dishes in Siesta Key, FL region?
The local cuisine in Siesta Key is influenced by its coastal location. You'll find plenty of fresh seafood restaurants serving dishes like grouper sandwiches, shrimp scampi, and stone crab claws. There are also many casual restaurants offering American classics like burgers and fries.
Destinations nearby
Best Siesta Key, FL holiday rentals with a balcony
8.6 7 reviews
Siesta Key, FL
04/07 – 08/07
SG$506/nighttotal: SG$2024 (4 )
Welcome To Your Happy Placeaka Where Real Life Takes A Vacation.
2 4
apartment , Siesta Key
This Siesta Key condo is conveniently located within a 2.4km walk of Crescent Beach and Siesta Key Beach, and 3.4km from Turtle Beach. This 121 square metre self-catering apartment sleeps six guests, boasting three bedrooms, two bathrooms, a terrace, swimming pool, jacuzzi, tennis court, and free Wi-Fi; nearby attractions include an on-site arcade.
This five-bedroom, three-bathroom holiday flat in Siesta Key offers exclusive beach access (#13) just across the street and is a mere 4-minute walk from entertainment, dining, and live music venues, with Point of Rocks reef located 60 metres away. This spacious accommodation, ideal for up to 18 guests, provides a car-free holiday experience with provided beach gear, including towels, chairs, umbrellas, bikes, and paddleboards, alongside secluded alfresco lounging areas and hammocks for relaxation.
9.5 105 reviews
Siesta Key, FL
31/08 – 02/09
SG$768/nighttotal: SG$1536 (2 )
Mandevilla | Pet Friendly Home Located In Siesta Key Village W/ Heated Pool, Walk To Beach!
1 2
apartment , Siesta Key
This Siesta Key house is located in the village, just a short distance from popular beaches, restaurants and attractions. It has received excellent ratings for location, cleanliness and overall user experience. The property offers a fully equipped kitchen, a comfortable living area and a laundry machine. Guests can enjoy outdoor grilling, a swimming pool, a terrace and a garden, making it a perfect place to relax and enjoy the Florida sunshine.
9.0 1 review
Siesta Key, FL
01/08 – 06/08
SG$474/nighttotal: SG$2370 (5 )
6415 Midnight Pass #707
2 5
house , Siesta Key
This Siesta Key holiday home, 6415 Midnight Pass #707, is a 7-minute walk from Crescent Beach, 2.6km from Turtle Beach, and 2.9km from Siesta Key Beach, offering convenient access to Siesta Key's famed sands. The 116 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, Jacuzzi, sauna, fitness centre, and tennis court, alongside a fully equipped kitchen and free Wi-Fi.
Best Siesta Key, FL holiday rentals with parking
10 44 reviews
Siesta Key, FL
04/07 – 11/07
SG$327/nighttotal: SG$2289 (7 )
102 M² House ∙ 2 Bedrooms ∙ 4 Guests
2 4
house , Siesta Key
This bayside apartment in the Midnight Cove 1 community on Siesta Key, Florida, offers easy walking access to Crescent Beach and is close to Siesta Key Village and Sarasota. The 102-square-metre (1100 sq ft) property sleeps four guests in two bedrooms and two bathrooms, boasting a gourmet kitchen, a private terrace, a swimming pool, and access to tennis courts; nearby attractions include discounted water sports rentals and free Siesta Key trolleys.
9.9 149 reviews
Siesta Key, FL
29/12 – 31/01
SG$479/nighttotal: SG$15807 (33 )
Siesta Key Gulf Front Condo
2 2
apartment , Siesta Key
This two-bedroom apartment is located in the Crescent Royale Condominiums on Siesta Key, just a short walk from the beach, widely considered the best in the USA. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. This 119 square metre apartment comfortably accommodates up to six guests. The property offers a range of amenities, including a swimming pool, Jacuzzi, fitness centre, and a private carport with dedicated parking.
9.3 19 reviews
Siesta Key, FL
04/07 – 11/07
SG$432/nighttotal: SG$3024 (7 )
Polynesian Gardens Villa: Renovated, Near Crescent Beach, Pool, Patio & Modern Comforts!
2 4
apartment , Siesta Key
This two-bedroom apartment is situated directly on the beach, just a 2.4 km walk from Siesta Key Beach and Crescent Beach, and within 1.6 km of Siesta Key Marina and St. Boniface Episcopal Church Labyrinth. The 104 square metre apartment offers a comfortable stay for up to four guests with amenities such as a swimming pool, a terrace, a garden, and free parking.
9.2 98 reviews
Siesta Key, FL
25/12 – 02/01
SG$551/nighttotal: SG$4408 (8 )
Siesta Key Condo: Resort Amenities, Walk To Beach!
2 5
house , Siesta Key
This Siesta Key apartment is located just 500 metres from Crescent Beach, a short drive from Siesta Key Beach and Turtle Beach, and within a 32-kilometre drive of the John and Mable Ringling Museum of Art. The apartment has been rated excellent for location, cleanliness and by previous guests. This two-bedroom apartment spans 84 square metres and comfortably accommodates up to six guests. The apartment offers a range of amenities including a swimming pool, spa, fitness centre, tennis court, and a private balcony with outdoor dining area.