Best Holiday rentals and Airbnb offers in Siesta Key, FL
8.6 14 reviews
Siesta Key, FL
20/06 – 27/06
SG$290/nighttotal: SG$2030 (7 )
Condo With Bay Views, Beach Access! - Midnight Cove Ii 137
2 2
apartment , Siesta Key
This Siesta Key apartment, situated in the Midnight Cove II complex, is a 0.64km walk from Siesta Key Beach and a 0.32km walk from a trolley stop providing easy access to Siesta Key Village. The 80 square metre self-catering property features two bedrooms (king and full with trundle bed), a fully equipped kitchen with granite countertops, and access to a heated pool, tennis/pickleball/racquetball/basketball courts, fitness centre, BBQ area, observation deck, and private docks.
10 134 reviews
Siesta Key, FL
01/01 – 31/03
SG$368/nighttotal: SG$32752 (89 )
Siesta Key Couple's Get Away!!!
1 2
apartment , Siesta Key
This Siesta Key apartment is situated less than 1.6km from Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offering easy access to pristine sands and watersports. The self-catering flat, sleeping two guests in one bedroom and one bathroom, includes a fully equipped kitchen, air conditioning, a swimming pool, and is within easy reach of St. Boniface Episcopal Church Labyrinth and Siesta Key Beach Playground.
9.4 7 reviews
Siesta Key, FL
04/07 – 08/07
SG$584/nighttotal: SG$2336 (4 )
2br Siesta Key Condo - Beach Access - Gbb 1340
2 4
apartment , Siesta Key
This recently updated two-bedroom, two-bathroom condo is situated in the Gulf and Bay - Bayside complex on Siesta Key, offering private beach access and proximity to Siesta Key's attractions. The second-floor apartment sleeps five, features a modern kitchen with granite countertops and appliances, two heated pools, tennis and pickleball courts, and a glassed lanai; enjoy the peaceful ambiance and easy access to the beach.
9.7 29 reviews
Siesta Key, FL
19/06 – 21/06
SG$1284/nighttotal: SG$2568 (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.
10 1 review
Siesta Key, FL
16/07 – 19/07
SG$353/nighttotal: SG$1059 (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 78 reviews
Siesta Key, FL
12/09 – 19/09
SG$251/nighttotal: SG$1757 (7 )
Sun And Sea Gem On Siesta Key
1 2
apartment , Siesta Key
This Siesta Key apartment, ideally located a short walk from the world-renowned Siesta Beach (ranked #2 in the US and #14 globally), offers easy access to Captain Curt's and various watersports rentals. Sleeping up to seven guests, this two-bedroom, two-bathroom condo boasts a fully equipped kitchen, a heated swimming pool, designated parking (#10), and modern interiors including smart TVs; nearby amenities include Tiki bars, ice cream shops and restaurants.
9.8 58 reviews
Siesta Key, FL
01/01 – 31/03
SG$461/nighttotal: SG$41029 (89 )
Shore Enough & More #3
1 2
apartment , Siesta Key
This newly renovated ground-floor apartment is situated on Siesta Key, less than 0.5 km from Siesta Key Beach and Siesta Key Village. The two-bedroom, one-bathroom condo sleeps six guests and features a king-size bed, two double beds, a fully equipped kitchen, and a shared laundry facility (small fee applies).
9.2 403 reviews
Siesta Key, FL
29/07 – 30/07
SG$881/nightfor 1 night
Shark Unit, Pool Jacuzzi Steps To Siesta Key Beach
1 5
apartment , Siesta Key
This Siesta Key property is located in Sarasota, just a stone's throw from the famous Siesta Key Beach and a short drive from Crescent Beach. The house has received excellent ratings for its location, cleanliness, and overall user experience. The property is a spacious house with a private pool and jacuzzi. Guests can enjoy a range of amenities, including a fully equipped kitchen, a terrace with sea views, a garden, and free parking and Wi-Fi.
8.7 3 reviews
Siesta Key, FL
21/07 – 26/07
SG$363/nighttotal: SG$1815 (5 )
Salt & Sun Siesta
1 4
apartment , Siesta Key
Salt & Sun Siesta is a holiday flat located in Sarasota, a 5-minute walk from Crescent Beach and 17.7 kilometres from the John and Mable Ringling Museum of Art. This 90 square metre apartment offers air-conditioned comfort for up to 7 guests, featuring 2 bedrooms, 2 bathrooms, a private terrace, an on-site restaurant, and an outdoor swimming pool.
This Siesta Key apartment is ideally located just 1.6 kilometres from Siesta Key Beach, offering easy access to the famous white sands and turquoise waters, as well as being close to St. Boniface Episcopal Church Labyrinth, Crescent Beach and Siesta Key Marina. The apartment has received very good user, location and cleanliness ratings, making it a popular choice for travellers. The apartment is spacious, covering 81 square metres and comfortably accommodating up to 6 guests in its two bedrooms and one bathroom. It offers a range of amenities, including a swimming pool, spa, fitness centre, tennis court, and barbecue grills, ensuring a comfortable and enjoyable stay.
9.5 33 reviews
Siesta Key, FL
09/07 – 11/07
SG$1054/nighttotal: SG$2108 (2 )
Minorga On The Gulf
1 4
house , Siesta Key
Minorga on the Gulf, a Siesta Key holiday home, is a 7-minute walk from Siesta Key Beach and within 9.6-16 kilometers of Sarasota attractions including the Ringling Museum of Art and Sarasota Opera House. This self-catering property boasts a fully equipped kitchen, swimming pool, free Wi-Fi, and private parking; it is suitable for adults aged 25 and over.
9.3 7202 reviews
Siesta Key, FL
31/10 – 07/11
SG$296/nighttotal: SG$2072 (7 )
Tropical Beach Resorts - Sarasota
1 4
resort , Siesta Key
Tropical Beach Resorts - Sarasota is situated on Siesta Key, just a short five-minute walk from the famous beach and a six-and-a-half-mile drive from downtown Sarasota and St. Armand's Circle. The resort has consistently received excellent ratings for its location, cleanliness, and overall user experience. This resort offers a range of amenities and activities, including a heated outdoor pool, complimentary beach chairs and towels, barbecue facilities, and a fitness centre. Guests can also enjoy shuffleboard, volleyball, scheduled yoga classes, and in-room conveniences like kitchenettes, free Wi-Fi, flat-screen TVs with DVD players, and iPod docking stations.
Best family friendly Siesta Key, FL holiday rentals
Among the 5754 accommodations in Siesta Key, FL, here are the 4 best family friendly rentals
9.7 76 reviews
Siesta Key, FL
04/07 – 07/07
SG$4122/nighttotal: SG$12366 (3 )
16 Guest Pool House Walk To The Beach And Village
6 1
apartment , Siesta Key
This Siesta Key house is situated just under 3 kilometres from Siesta Key Beach, and within 5 kilometres of both Shell Beach and Crescent Beach. It is located in Siesta Key Village, a quiet and relaxing area, offering a peaceful retreat from the hustle and bustle of more crowded areas. Guests have rated this property excellent for location, cleanliness and overall experience. The property is a 6-bedroom house that provides ample space for large families or groups of friends. It offers modern amenities, including free Wi-Fi, a fully equipped kitchen, a private pool, a fenced private yard, and barbecue grills.
9.2 40 reviews
Siesta Key, FL
21/06 – 28/06
SG$668/nighttotal: SG$4676 (7 )
Beautiful 2025 Renovated - 550 Sq Ft Patio - Across Street From Beach
2 3
apartment , Siesta Key
This beachfront Siesta Key condo offers direct access to Siesta Key Beach, a short walk from St. Boniface Episcopal Church Labyrinth and within 3.2km of Crescent Beach and Siesta Key Beach Playground. The 164 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a private pool, fully equipped kitchen, fitness centre, sauna, and tennis court.
9.7 189 reviews
Siesta Key, FL
01/08 – 08/08
SG$401/nighttotal: SG$2807 (7 )
Siesta Key Dream Vacation
2 2
apartment , Siesta Key
This two-bedroom apartment is located on Siesta Key, just a 5-minute walk from Crescent Beach and 2 kilometres from Siesta Key Beach. The apartment is highly rated by previous guests, with excellent scores for location, cleanliness, and overall experience. The 130 square metre apartment comfortably accommodates up to 6 guests and features a fully equipped kitchen, a private pool, a terrace, and a garden. The apartment also has a range of amenities including air conditioning, Wi-Fi, a washing machine, and a dryer, as well as free parking.
8.6 10 reviews
Siesta Key, FL
19/06 – 21/06
SG$683/nighttotal: SG$1366 (2 )
Florida Charm, Bayside, Pool, Tiki, Steps To Beach
2 4
apartment , Siesta Key
This Siesta Key beachfront apartment is located near Siesta Key Beach and Crescent Beach, within 2km of St Boniface Episcopal Church Labyrinth, Siesta Key Beach Playground, and Siesta Key Marina. The 70 square metre property offers two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, spa, and concierge services.
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
9.5 112 reviews
Siesta Key, FL
23/12 – 28/12
SG$395/nighttotal: SG$1975 (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.
9.8 161 reviews
Siesta Key, FL
21/07 – 24/07
SG$375/nighttotal: SG$1125 (3 )
Cottage On Siesta Key
Beachside & Stunning Sunsets
1 2
cottage , Siesta Key
This Siesta Key apartment is just a short walk from Crescent Beach, a popular beach known for its soft, white sand, and is close to shops, restaurants, and cafes. It receives excellent ratings for location, cleanliness, and overall user experience. The apartment has one bedroom and one bathroom and can accommodate up to four guests. It offers a range of amenities including a kitchen with a fridge, freezer, microwave, and dishwasher, a swimming pool, a garden, parking, and free Wi-Fi.
9.8 58 reviews
Siesta Key, FL
22/06 – 27/06
SG$513/nighttotal: SG$2565 (5 )
Siesta Villa Laughing Gull
2 2
house , Siesta Key
This house is located in Siesta Key, within walking distance of Crescent Beach and a short drive from Siesta Key Beach. It has received excellent ratings for location, cleanliness, and overall user experience. The house has three bedrooms and can accommodate up to five guests. You can enjoy features such as a fully equipped kitchen, air conditioning, a private terrace, a swimming pool, and free parking.
9.2 49 reviews
Siesta Key, FL
06/07 – 13/07
SG$212/nighttotal: SG$1484 (7 )
Bay View Condo, Minutes To Top Beach In The Us
2 2
apartment , Siesta Key
This Siesta Key beachfront apartment offers stunning views and is a short walk (less than 2.4km) from both Siesta Key Beach and Crescent Beach, with Turtle Beach a 4.5km drive away. The two-bedroom, one-bathroom flat sleeps four guests and includes air conditioning, a swimming pool, parking, and complimentary Wi-Fi; enjoy the smoke-free environment and direct waterfront access.
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
10 3 reviews
Siesta Key, FL
08/07 – 14/07
SG$487/nighttotal: SG$2922 (6 )
Peaceful Siesta Key Condo - Short Stroll To The Beach - Gbb 1219
2 4
apartment , Siesta Key
This beachfront apartment is situated near Siesta Key Beach, a 15-minute walk from St. Boniface Episcopal Church Labyrinth and under 3.2km from Crescent Beach. This 119 square metre, two-bedroom, two-bathroom property sleeps four, boasting a fully equipped kitchen, private terrace, swimming pool, sauna, fitness centre, tennis court, and free Wi-Fi; BBQ facilities are also available.
9.7 117 reviews
Siesta Key, FL
04/07 – 07/07
SG$847/nighttotal: SG$2541 (3 )
Palm Bay 5th Floor On The Beach \Nsunsets From The Open Lanai, Two Queen Beds.
1 1
apartment , Siesta Key
This Siesta Key beachfront apartment, less than 1.6km from Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offers direct beach access and proximity to local attractions. The one-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, swimming pool, Jacuzzi, fitness centre, tennis court, and spa, plus on-site parking.
9.0 4 reviews
Siesta Key, FL
19/07 – 01/08
SG$346/nighttotal: SG$4498 (13 )
Condo# 410- Beautiful
2 4
apartment , Siesta Key
This Siesta Key condo, situated within La Siesta Condominiums, offers easy walking access to Siesta Village and Siesta Key Public Beach. The 81 square metre (870 square foot) apartment features two bedrooms, one bathroom, sleeps six, and includes access to a swimming pool, tennis court, and fitness centre, plus a screened lanai.
Siesta Key, FL
17/06 – 26/06
SG$574/nighttotal: SG$5166 (9 )
Lovely 2bd Condo Close To The Beach (An1145)
2 6
apartment , Siesta Key
This private eighth-floor condominium in Siesta Key's South Village offers direct access to Crescent Beach, just across the street, and is a short walk from Siesta Key Beach and Siesta Key Village, with complimentary trolley service available. This two-bedroom, two-bathroom apartment accommodates up to six guests and features a fully equipped kitchen, air conditioning, a swimming pool, a balcony with north-western views, and includes four beach chairs, towels, an umbrella, a cooler, and a beach cart for your convenience.
This Siesta Key apartment, located in the La Siesta Condominiums, is steps from Siesta Key Beach and a short walk from Siesta Village. The 81-square-metre (870 sq ft) property offers two bedrooms, one bathroom, sleeps up to six guests, and includes a fully equipped kitchen, private Wi-Fi, and access to a swimming pool, fitness centre, and tennis court.
9.8 241 reviews
Siesta Key, FL
21/07 – 24/07
SG$453/nighttotal: SG$1359 (3 )
Clean, Modern And Newly Renovated Condo On Us #1 Private Siesta Key Beach
1 2
apartment , Siesta Key
This Siesta Key apartment is situated less than 2km from Siesta Key Beach and Crescent Beach, also within 1.6km of Siesta Key Marina and St Boniface Episcopal Church Labyrinth. Offering a one-bedroom, one-bathroom flat with a private pool, free WiFi, fully equipped kitchen, and access to a shared garden and barbecue facilities, this pet-friendly property sleeps up to two guests and includes a patio and Smart TV.
9.3 727 reviews
Siesta Key, FL
25/10 – 01/11
SG$255/nighttotal: SG$1785 (7 )
Crescent Beach 1011 #3
1 2
house , Siesta Key
This charming house is located directly on Crescent Beach in Siesta Key, just a short drive from Turtle Beach. It has received excellent ratings for location, cleanliness and overall experience. The house has two bedrooms, a living room, a fully equipped kitchen and two bathrooms. It features air conditioning, a dishwasher, a TV and a private swimming pool, as well as a terrace and a garden.
8.7 908 reviews
Siesta Key, FL
19/06 – 21/06
SG$1060/nighttotal: SG$2120 (2 )
The Ringling Beach House
2 6
resort , Siesta Key
The Ringling Beach House is directly opposite the world-renowned Siesta Key Beach, with the lively Siesta Key Village just an 8-minute walk away, offering a perfect blend of beachside relaxation and easy access to shops and restaurants. This apartment complex has consistently received very good ratings for cleanliness and user experience, and an excellent rating for its location. Each apartment is individually decorated with a choice of leather, dark wood, or patterned furnishings, creating a unique and comfortable atmosphere. Guests can enjoy a refreshing outdoor community pool, barbecue facilities, and complimentary beach chairs, making it easy to relax and enjoy the beautiful Florida weather.