Holiday Rentals in Siesta Key, FL

7731 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Siesta Key, FL holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

New Listing! The Village Breeze 6br With Heated Pool, Near Beach, 250ft To Siesta Key Village! - Siesta Key, FL
10 2 reviews

New Listing! The Village Breeze 6br With Heated Pool, Near Beach, 250ft To Siesta Key Village!

apartment, Siesta Key
This six-bedroom, five-bathroom Siesta Key Village holiday home is situated 76 metres from the village centre and a short walk from Siesta Key Beach.
Sleeping up to 21 guests, this recently remodelled (May 2025) property boasts a heated pool, ample parking, and comprises three adjoining two-bedroom units, each with a fully equipped kitchen including a dishwasher, microwave and fridge, plus free internet access; it's ideally located for exploring Siesta Key's restaurants, bars and water sports.
Honeysuckle | Just Steps From Siesta Key Village! - Siesta Key, FL
No reviews

Honeysuckle | Just Steps From Siesta Key Village!

apartment, Siesta Key
This Siesta Key apartment is located in Siesta Key Village, 0.1 kilometres from local shops and dining, and a 3-minute walk to Siesta Key Beach.
This spacious accommodation sleeps up to 12 guests across two adjacent ground-level units, offering dual kitchens, living areas, and access to a shared heated pool, with the surrounding area providing numerous options for beach bars, live music venues, and watersports.
Harbor Towers – Bayfront Luxury With Pool & Tennis - Siesta Key, FL
No reviews

Harbor Towers – Bayfront Luxury With Pool & Tennis

apartment, Siesta Key
This Sarasota flat is a 7-minute walk from Crescent Beach and 17.7 kilometres from the John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport.
This 130-square-metre accommodation sleeps up to 11 guests across two bedrooms and two bathrooms, featuring a swimming pool, tennis court, sauna, and complimentary Wi-Fi.
Beachfront Siesta Key - 3 Night Min W/beach Gear! - Siesta Key, FL
10 70 reviews

Beachfront Siesta Key - 3 Night Min W/beach Gear!

apartment, Siesta Key
Sea Shell Condos, Unit #105, offers a beachfront apartment directly on Siesta Key Beach, steps from the shoreline and across the street from restaurants including Captain Curt's and Sniki Tiki.
This two-bedroom, two-bathroom holiday flat sleeps six, featuring a fully equipped kitchen, king-size master bed, two double beds, a queen-size sofa bed, on-site laundry, and access to a communal swimming pool; beach equipment (chairs, umbrellas, toys, towels and a cooler) is provided.

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 Key Dream Inn Rental - Close To Village! - Siesta Key, FL
10 64 reviews

Siesta Key Dream Inn Rental - Close To Village!

studio, Siesta Key
This Siesta Key studio apartment is situated 0.5 kilometres from Siesta Key Beach and close to Siesta Key Village, offering easy access to restaurants and entertainment.
The self-catering unit sleeps four, features a fully equipped kitchen with dishwasher, a private balcony, keyless entry, shared laundry facilities, and includes beach gear for guest use.
Shore Enough #4 - Siesta Key, FL
9.4 23 reviews

Shore Enough #4

apartment, Siesta Key
This Siesta Key condo is situated 0.4 km from Siesta Key Village and a short 0.24 km stroll from Siesta Key's renowned beach.
The two-bedroom, one-bathroom apartment sleeps four, offering a shared pool, parking, and is fully equipped with a fridge and microwave; nearby amenities include ice cream parlours, coffee shops and pizzerias.
Minorga Sand Dollar On The Key - Siesta Key, FL
9.5 127 reviews

Minorga Sand Dollar On The Key

house, Siesta Key
Minorga On the Key is located just 800 metres from Siesta Key Beach and 2.4 kilometres from Crescent Beach, with the John and Mable Ringling Museum of Art 15 kilometres away and Sarasota Opera 10 kilometres away. The property has received excellent ratings for location, cleanliness and overall experience.
The house features a well-equipped kitchen with a fridge, microwave oven, and dishwasher, as well as a comfortable seating area. This Siesta Key holiday home also offers free Wi-Fi, satellite TV, a washing machine, air conditioning, a private swimming pool, a garden, and private parking.
Stroll To Siesta Beach From Serene Condo - Siesta Key, FL
9.2 92 reviews

Stroll To Siesta Beach From Serene Condo

apartment, Siesta Key
This one-bedroom house is located in Siesta Key, just a 15-minute walk from both Siesta Key Beach and Crescent Beach. It's also within 2km of Siesta Key Marina and St. Boniface Episcopal Church Labyrinth. The house has received excellent ratings for location, cleanliness, and user experience.
This comfortable property can accommodate up to four guests and features a fully equipped kitchen, a private pool, a terrace, and a garden. Enjoy amenities such as free Wi-Fi, air conditioning, and a washing machine and dryer.

Frequently asked questions about holiday rentals in Siesta Key, FL

Popular destinations

Best Siesta Key, FL holiday rentals with a balcony

Peaceful Siesta Key Condo - Short Stroll To #1 Beach - Siesta Key, FL
10 1 review

Peaceful Siesta Key Condo - Short Stroll To #1 Beach

house, Siesta Key
This Siesta Key condo, a short walk from Crescent Beach and within 17.7km of the Ringling Museum of Art and Sarasota Bradenton International Airport, offers convenient access to Siesta Key's renowned beaches.
This 119 square metre property boasts two bedrooms, two bathrooms, sleeping four guests, and features a private balcony, sauna, fitness centre, and tennis court, all within easy reach of local attractions.
[Lounge Like Locals] Walk To Siesta Beach +Bikes - Siesta Key, FL
9.8 36 reviews

[Lounge Like Locals] Walk To Siesta Beach +Bikes

apartment, Siesta Key
This Siesta Key apartment, a short 1-2 kilometre walk from Siesta Key Public Beach and the Siesta Key Farmers' Market, offers convenient access to local attractions.
The two-bedroom, one-bathroom property sleeps four guests and includes amenities such as Wi-Fi, on-site parking, and in-unit laundry facilities, plus access to on-site bicycles.
177 M² House ∙ 3 Bedrooms ∙ 8 Guests - Siesta Key, FL
9.8 23 reviews

177 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Siesta Key
Peacock Villa is located on Siesta Key, less than 800 metres from the lively Siesta Key Village and a short walk from the beach. Guests have consistently rated this property as excellent.
The three-bedroom villa is spread over three floors, offering 176 square metres of space for up to eight guests. The property includes a private swimming pool, a cabana room, a ping pong table, and a full kitchen, as well as a private elevator and two balconies.
Luxury Private Condo On The Anchorage, Siesta Key Condo 1024 - Siesta Key, FL
9.5 104 reviews

Luxury Private Condo On The Anchorage, Siesta Key Condo 1024

apartment, Siesta Key
This charming two-bedroom house is conveniently located in Siesta Key, just a short walk from both Siesta Key Marina and Crescent Beach, and a short distance from the famous Siesta Key Beach. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The house comfortably accommodates up to six guests and offers a range of amenities including a fully equipped kitchen, a private swimming pool, a tennis court, and a spa. Guests can enjoy a relaxing stay with access to a garden, a terrace, and a fitness centre, and can explore the island's many attractions, including boat rentals, fishing charters, and dolphin watching tours.

Best Siesta Key, FL holiday rentals with parking

Cjs - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach! - Siesta Key, FL
No reviews

Cjs - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach!

house, Siesta Key
This pet-friendly holiday home in Bailey Hall, Siesta Key, offers an exceptional location, situated just a 1-minute walk from Siesta Key Beach and approximately 10.3 kilometres from Marina Jack and Sarasota Opera.
This spacious property boasts 6 bedrooms and 6 bathrooms, accommodating up to 40 guests with amenities including a fully equipped kitchen, air conditioning, a spa, and Wi-Fi, alongside 24-hour front desk service.
Beautiful Apartment With First Class Amenities On The Anchorage, Siesta Key Apartment 1019 - Siesta Key, FL
9.4 91 reviews

Beautiful Apartment With First Class Amenities On The Anchorage, Siesta Key Apartment 1019

apartment, Siesta Key
This apartment is located in Siesta Key, just 0.9 kilometres from the renowned Siesta Key Beach, within a 10-minute walk of Siesta Key Marina and Crescent Beach. The apartment has received excellent ratings for location and user experience, with a very good rating for cleanliness.
This two-bedroom, two-bathroom apartment offers 116 square metres of space, comfortably accommodating up to six guests. The apartment includes a well-equipped kitchen, a relaxing balcony, air conditioning, a swimming pool, a sauna, a spa, a fitness centre, a tennis court, and parking.
Beechwood Suites A - Siesta Key, FL
10 85 reviews

Beechwood Suites A

apartment, Siesta Key
This designer two-bedroom apartment on Siesta Key is situated approximately 0.8km from Crescent Beach, Siesta Key's renowned beach.
The 2-bathroom property sleeps six, boasts a kitchen with dishwasher, offers air conditioning, a swimming pool, and is near restaurants, Earth Origins Market, and water activity rental options.
[Beach Elements] Pool View + Private Beach & Bikes - Siesta Key, FL
9.6 346 reviews

[Beach Elements] Pool View + Private Beach & Bikes

apartment, Siesta Key
This Siesta Key apartment is just a short walk (around 0.5km) from the beautiful beach and a short drive (around 2km) from the bustling Siesta Key Village. The apartment consistently receives excellent ratings for its location, cleanliness, and overall user experience.
This studio apartment can accommodate up to three guests and features a fully equipped kitchen with granite countertops and stainless steel appliances. Enjoy the convenience of a private patio, community BBQ area, laundry facilities, and beach cruiser bike rentals (for an additional fee), as well as provided beach chairs and other amenities.
©2026 cozycozy.com