Holiday Rentals in Siesta Key, FL

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Siesta Key, FL holiday rentals
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7731 Holiday Rentals and Airbnb in Siesta Key, FL

Best family friendly Siesta Key, FL holiday rentals

Among the 7731 accommodations in Siesta Key, FL, here are the 4 best family friendly rentals

Siesta Key Beach Front 2 Bedroom  Condo W/ Parking - Siesta Key, FL
9.9 63 reviews

Siesta Key Beach Front 2 Bedroom Condo W/ Parking

apartment, Siesta Key
This Siesta Key apartment is located just a short walk from the famous white sand beaches and within easy reach of the town centre. It has received excellent ratings for cleanliness, location and user experience. The apartment is a two-bedroom, two-bathroom property suitable for up to four guests. It comes with a fully equipped kitchen, air conditioning, a garden and parking, as well as access to golf cart transportation.
Siesta Beach Getaway - Minutes To Beach, Shops, Dining - Siesta Key, FL
9.0 30 reviews

Siesta Beach Getaway - Minutes To Beach, Shops, Dining

apartment, South Sarasota
This renovated three-bedroom apartment is located in South Sarasota, just a few kilometres from Siesta Key Beach, a world-renowned beach known for its soft white sand and calm waters. This property has received excellent user ratings, making it a popular choice for travellers.
The apartment is spacious and open, with a floor area of 130 square metres and a capacity of eight guests. It offers a fully equipped kitchen, a private garden, parking, and air conditioning, as well as a comfortable living area and bedrooms.
Steps To 2025 #1 Rated Beach In Usa Fun-n-sun Modern 2+2 Condo Pool Pickleball - Siesta Key, FL
10 62 reviews

Steps To 2025 #1 Rated Beach In Usa Fun-n-sun Modern 2+2 Condo Pool Pickleball

apartment, Siesta Key
This apartment is located directly across from Siesta Beach, less than 1.6km from Siesta Village and 11km from downtown Sarasota. It has been rated excellent by previous guests.
The property has two bedrooms and a floor area of 158 square metres. This self-catering apartment offers a fully-equipped kitchen, a terrace, a swimming pool, a spa, parking and a garden.
Crystal House On Siesta Key Beach - Siesta Key, FL
9.8 146 reviews

Crystal House On Siesta Key Beach

apartment, Siesta Key
This Siesta Key apartment, situated directly across from the Gulf of Mexico beach, offers unparalleled access to the sands and boasts a private dock on Sarasota Bay.
The two-bedroom suite sleeps six, features a fully equipped kitchen with stainless steel appliances, a heated pool, and complimentary amenities including Segway Ninebot scooters, an Xbox, and GAIA premium toiletries.

Best Siesta Key, FL holiday rentals with a pool

Among the 7731 accommodations in Siesta Key, FL, here are the 4 best rentals with a pool

Siesta Paradise - Siesta Key, FL
10 14 reviews

Siesta Paradise

apartment, Siesta Key
This new two-bedroom, two-bathroom apartment in a sought-after Siesta Key district offers excellent access to Siesta Key Beach and Siesta Key Village.
This immaculate accommodation, designed for up to six guests, boasts a whole-house water filtration system, air conditioning, a swimming pool, a sauna, and a fitness centre, with a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
Unit 142 - 1 Bedroom 1 1/2 Bathroom Club Side Interior Condomimium - Siesta Key, FL
9.6 31 reviews

Unit 142 - 1 Bedroom 1 1/2 Bathroom Club Side Interior Condomimium

apartment, Siesta Key
This Siesta Key Palm Bay Club condo, a two-minute walk from a private beach, pool, tennis courts, and gym, offers convenient access to Siesta Key's amenities.
This 90 square metre (969 square foot) apartment features one bedroom with two queen beds, two bathrooms, a spacious living area with a 55" smart TV, and a fully equipped kitchen, comfortably sleeping four guests and boasting modern amenities including a private balcony and a half-bath.
Updated Siesta Key Vacation Rental At Bay Oaks - Siesta Key, FL
9.4 21 reviews

Updated Siesta Key Vacation Rental At Bay Oaks

apartment, Siesta Key
This Siesta Key condo, situated in the Bay Oaks community, is under a kilometre from Siesta Key's public beach, 0.8km from South Village, and 3.2km from Siesta Key Village.
The two-bedroom, two-bathroom apartment sleeps five, boasts a fully equipped kitchen, in-unit laundry, a private carport space, and access to a heated pool, tennis courts, and a clubhouse within the Bay Oaks complex.
Condo# 409  Steps From Siesta Key Beach Condo - Siesta Key, FL
9.4 24 reviews

Condo# 409 Steps From Siesta Key Beach Condo

apartment, Siesta Key
This Siesta Key condo is situated less than 1.6km from Siesta Key Beach, close to Siesta Key Beach Playground, St Boniface Episcopal Church Labyrinth, and the Siesta Key Farmers Market.
The 76 square metre apartment features one bedroom, one bathroom, sleeps four, and includes a private pool, fitness centre access, on-site parking, and a fully equipped kitchen with appliances such as a fridge, microwave, and dishwasher.

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Best Siesta Key, FL holiday rentals with a balcony

A  Gem On Siesta Key Close To Village - 2br W Balcony,  1945 Triplex 2nd Floor - Siesta Key, FL
9.6 140 reviews

A Gem On Siesta Key Close To Village - 2br W Balcony, 1945 Triplex 2nd Floor

apartment, Siesta Key
This family-friendly holiday home is located on Siesta Key, just a short distance from Siesta Key Beach, Irma Beach, and St. Boniface Episcopal Church Labyrinth. The property has excellent user ratings and is perfect for families looking for a comfortable and enjoyable stay.
The two-bedroom house, covering 121 square metres, can accommodate up to six guests. It offers a range of amenities, including a kitchen, a terrace, a garden, a spa, and parking, as well as concierge services, free Wi-Fi, and a sofa bed.
2 Bedroom 2 Bathroom Gulf Front Condominium. - Siesta Key, FL
9.6 29 reviews

2 Bedroom 2 Bathroom Gulf Front Condominium.

apartment, Siesta Key
This 121 square metre, two-bedroom, two-bathroom beachfront condominium in Siesta Key, located on the 8th floor of the Grande Tower, offers direct Gulf of Mexico views and is a 1.6 kilometre walk from Siesta Key Beach and Crescent Beach.
This apartment features a fully equipped kitchen, an enclosed patio, a swimming pool, and is within a 7 kilometre radius of St. Armands Circle and the Mall at University Town Centre, accommodating up to six guests.
Spacious 2br Siesta Key Condo With Private Beach Access - Siesta Key, FL
9.8 4 reviews

Spacious 2br Siesta Key Condo With Private Beach Access

house, Siesta Key
This Siesta Key condo, a seven-minute walk from Crescent Beach, is conveniently located 17.7km from the Ringling Museum and Sarasota Bradenton International Airport.
The 111-square-metre property boasts two bedrooms, two bathrooms, sleeps four, and includes a private balcony, sauna, fitness centre, tennis court, parking, and free Wi-Fi.
Condo# 420 2 Bed/1 Bath Condo Steps To Siesta Key Beach! - Siesta Key, FL
9.3 8 reviews

Condo# 420 2 Bed/1 Bath Condo Steps To Siesta Key Beach!

apartment, Siesta Key
This two-bedroom apartment is situated in Siesta Key, just a short walk from Siesta Key Beach, consistently ranked among the world's best beaches, and a short distance from Siesta Village.
This 74 square metre apartment is perfect for a family holiday, comfortably sleeping up to five guests and boasting a fully equipped kitchen, a screened-in lanai, and access to a swimming pool, fitness centre and tennis court.

Best Siesta Key, FL holiday rentals with parking

16 Guest Pool House Walk To The Beach And Village - Siesta Key, FL
9.7 89 reviews

16 Guest Pool House Walk To The Beach And Village

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.
Beach Club | Heated Pool | Walk To Crescent Beach With Gated Access Poolside | Updated Condo - Siesta Key, FL
9.4 180 reviews

Beach Club | Heated Pool | Walk To Crescent Beach With Gated Access Poolside | Updated Condo

apartment, Siesta Key
This beachfront apartment is located on Siesta Key, just a short distance from Crescent Beach and Siesta Key Beach, and within easy reach of Siesta Key Marina and Point of Rocks, making it ideal for exploring the island. The property enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment features two bedrooms and spans 71 square metres, offering ample space for a relaxing holiday. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, garden and spa, as well as free parking and internet access.
Siesta Key Sanctuary -Pool-kayaks-tikihut-king Bed - Siesta Key, FL
9.6 8 reviews

Siesta Key Sanctuary -Pool-kayaks-tikihut-king Bed

cottage, Siesta Key
This charming cottage is situated within the Solitude Suites on Siesta Key, a small resort just a short walk from the renowned Siesta Key Beach. The cottage offers a peaceful escape, providing a tranquil retreat amidst the vibrant atmosphere of the surrounding area.
The cottage is a one-bedroom property, comfortably accommodating four guests. It features a fully equipped kitchen, a private screened lanai, and access to shared resort amenities including a pool, kayaks, paddle boards, and a Tiki Hut.
The Beach Club At Siesta #106b - Siesta Key, FL
No reviews

The Beach Club At Siesta #106b

house, Siesta Key
This holiday cottage is situated in Point O'Rocks, mere steps from Crescent Beach, and 17.7 kilometres from the John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 75 square metre, two-bedroom holiday home accommodates up to 11 guests and features a fully equipped kitchen, private patio, access to a shared heated swimming pool, hot tub, fitness room, and complimentary WiFi and parking.
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