Holiday Rentals in Sarasota, FL

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Sarasota, FL holiday rentals
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3210 Holiday rentals and Airbnb in Sarasota, FL

Best family friendly Sarasota, FL holiday rentals

Among the 3210 accommodations in Sarasota, FL, here are the 4 best family friendly rentals

Apartment ∙ 2 Bedrooms ∙ 6 Guests - Sarasota, FL
Sarasota, FL
29/06 – 17/07
228 â‚¬/nighttotal: 4104 â‚¬ (18 )

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 6
apartment , Siesta Key
This Siesta Key lagoon-view property is located a short walk from restaurants such as the Orange Octopus and Daiquiri Deck, and a 0.96km stroll or a shorter bike ride from Siesta Key Beach.
The self-catering apartment offers a 150-square-foot private balcony with lagoon views, two bedrooms (one king, two single beds) plus a sofa bed sleeping up to six guests, a well-equipped kitchen, and access to a heated pool, BBQ areas, tennis and pickleball courts.
Charming 2 Bedroom 2 Bathroom Home With Pool In Sarasota  With Central Location. - Sarasota, FL
9.4 35 reviews
Sarasota, FL
26/06 – 28/06
263 â‚¬/nighttotal: 526 â‚¬ (2 )

Charming 2 Bedroom 2 Bathroom Home With Pool In Sarasota With Central Location.

2 2
apartment , Kensington Park
This two-bedroom, two-bathroom Sarasota apartment in Kensington Park offers convenient access to Downtown Sarasota (approx. 16km), Sarasota Bradenton International Airport (approx. 19km), UTC Mall (approx. 21km), and Sarasota Memorial Hospital (approx. 21km), as well as Lido Key and Siesta Key beaches (approx. 32km and 40km respectively).
The self-catering flat sleeps six, features a swimming pool, Jacuzzi, parking, and includes a fridge, microwave, and dishwasher; nearby attractions include Marie Selby Botanical Gardens and Sarasota Jungle Gardens.
Cosmopolitan Suite, Centrally Located To Downtown And The Beach. - Sarasota, FL
10 14 reviews
Sarasota, FL
27/06 – 04/07
254 â‚¬/nighttotal: 1778 â‚¬ (7 )

Cosmopolitan Suite, Centrally Located To Downtown And The Beach.

2 2
apartment , Sarasota
This two-bedroom apartment is ideally situated in Sarasota, just a short distance from the Sarasota Opera and the John and Mable Ringling Museum of Art. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment comfortably accommodates up to four guests and is equipped with a fully fitted kitchen, a private terrace, and a garden. Enjoy a range of amenities including free parking, Wi-Fi, and air conditioning, as well as access to a swimming pool and a concierge service.
Tropical Heart Villa Is Walking Distance To Downtown And A 5 Min Drive To Beach! - Sarasota, FL
10 5 reviews
Sarasota, FL
03/07 – 05/07
333 â‚¬/nighttotal: 666 â‚¬ (2 )

Tropical Heart Villa Is Walking Distance To Downtown And A 5 Min Drive To Beach!

2 4
house , Sarasota
This Sarasota holiday home is situated in the Laurel Park neighbourhood, a short drive from downtown Sarasota's attractions and Lido Beach and Siesta Key Beach.
The two-bedroom, one-bathroom villa sleeps six, features a private garden, and includes amenities such as a fridge, microwave, dishwasher, air conditioning, and parking; nearby attractions include Marie Selby Botanical Gardens and Sarasota Jungle Gardens.

Best Sarasota, FL holiday rentals with a pool

Among the 3210 accommodations in Sarasota, FL, here are the 4 best rentals with a pool

Luxury Condo Living On Sarasota Bay, Minutes From Downtown - Admirals Watch - Sarasota, FL
9.6 5 reviews
Sarasota, FL
01/11 – 30/11
129 â‚¬/nighttotal: 3741 â‚¬ (29 )

Luxury Condo Living On Sarasota Bay, Minutes From Downtown - Admirals Watch

1 4
apartment , Sarasota
This centrally located Sarasota condo is within 1.6km of the Marietta Museum of Art and Whimsy and Ringling College of Art and Design, and under 1.6km from the Van Wezel Performing Arts Hall and Sarasota County Visitor Information Center and History Museum.
The 80 square metre apartment sleeps four, offering one bedroom, two bathrooms, a fully equipped kitchen, free Wi-Fi, a private balcony, and access to an on-site fitness centre, swimming pool, and jacuzzi.
Exquisite Bungalow With Shared Pool, Washer & Dryer, And Wifi - Sarasota, FL
Sarasota, FL
19/07 – 26/07
232 â‚¬/nighttotal: 1624 â‚¬ (7 )

Exquisite Bungalow With Shared Pool, Washer & Dryer, And Wifi

3 6
apartment , Sarasota
This three-bedroom, two-bathroom apartment is situated in Sarasota's Bayou Oaks neighbourhood, offering convenient access to St. Armands Circle and the Mall at University Town Centre, and is a short drive from Lido Beach and Siesta Key Beach.
This 97-square-metre flat accommodates up to six guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a terrace or balcony, and parking, with pets welcome and WiFi provided.
Tivoli By The Sea - Sarasota, FL
Sarasota, FL
30/08 – 06/09
1270 â‚¬/nighttotal: 8890 â‚¬ (7 )

Tivoli By The Sea

7 20
apartment , Siesta Key
Tivoli by the Sea apartments offer self-catering accommodation a 5-minute walk from Siesta Key Beach, approximately 17.7 kilometres from the Ringling Museum of Art in Sarasota.
Each air-conditioned apartment includes a fully equipped kitchen with oven, microwave and dishwasher, a private entrance, outdoor seating, a TV, and access to a swimming pool and tennis court.
Charming Gillespie Park Bungalow With Pool - Sarasota, FL
9.9 14 reviews
Sarasota, FL
20/12 – 03/01
306 â‚¬/nighttotal: 4284 â‚¬ (14 )

Charming Gillespie Park Bungalow With Pool

2 2
apartment , Sarasota
This 1925 bungalow is situated in Sarasota's Gillespie Park district, just 50 metres from Gillespie Park and a short distance from Downtown Sarasota's amenities, with Lido Beach and St. Armands Circle less than 7.2 kilometres away.
This two-bedroom, two-bathroom flat accommodates up to five guests and offers a private heated swimming pool, a dedicated sunroom, and a butler's pantry, along with on-site laundry facilities and Wi-Fi.

Frequently asked questions about holiday rentals in Sarasota, FL

  • What should a first-time visitor not miss in Sarasota, FL?

    For a first-timer, you absolutely must visit the Ringling Museum of Art, with its stunning collection and beautiful grounds. Then, head over to Siesta Key Beach, which is consistently ranked as one of the best beaches in the US, with its white, powdery sand.
  • What are the best Airbnb and holiday rentals in Sarasota, FL?

  • Which neighborhood in Sarasota, FL should you consider for a vacation rental?

    For a vacation rental, I'd recommend the neighbourhood of Siesta Key. It's a popular choice for families and couples, offering a range of rental options, from beachside condos to charming cottages. You'll be close to the beach and have easy access to restaurants and shops.
  • What are the most popular Airbnbs in Sarasota, FL?

  • What are the top family-friendly attractions in Sarasota, FL?

    Sarasota is great for families! The Mote Marine Laboratory & Aquarium is a must-see for kids of all ages, with its fascinating exhibits on marine life. The Children's Garden at Selby Gardens is another great option, offering a fun and educational experience with its interactive displays.
  • What are the best holiday rentals with a pool in Sarasota, FL?

  • When is the best time to book a vacation rental in Sarasota, FL?

    The best time to book a vacation rental in Sarasota is during the shoulder seasons, from April to May and September to October. You'll find great deals and fewer crowds compared to the peak season, which runs from June to August.
  • What are the best rentals for families and kids in Sarasota, FL?

  • What events or festivals should visitors check out in and around Sarasota, FL?

    The Sarasota Film Festival is a popular event that attracts film enthusiasts from around the world. You can also catch the Sarasota Chalk Festival, a vibrant street art festival that transforms the city into a canvas of colourful chalk drawings.
  • What are the best rentals or Airbnbs with a jacuzzi in Sarasota, FL?

  • What are the best budget-friendly activities in Sarasota, FL?

    Sarasota has plenty of free activities! Take a stroll along the scenic Bayfront, enjoy a picnic at the Lido Key Beach, or explore the exhibits at the Sarasota Art Museum of New College. You can also visit the Marie Selby Botanical Gardens, which offers free admission on Tuesdays.
  • What are the best restaurants with local dishes in Sarasota, FL?

    For a taste of local cuisine, I recommend checking out The Old Salty Dog, a waterfront restaurant known for its fresh seafood. You can also try the award-winning seafood at Owen's Fish Camp, which has been a local favourite for decades.
  • What are the best walking or cycling routes in Sarasota, FL?

    The Legacy Trail is a great option for both walking and cycling. It's a paved, multi-use trail that stretches for 13 kilometres, offering scenic views of the area. You can also explore the scenic Bayfront Trail, which winds along the waterfront and offers stunning views of the bay.
  • Are there pet-friendly attractions in Sarasota, FL?

    Absolutely! Many of the beaches in Sarasota are dog-friendly, including Brohard Paw Park, which is specifically designed for dogs. Many local restaurants also have outdoor seating areas where you can bring your furry friend.
  • What are the benefits of choosing a vacation rental in Sarasota, FL?

    Vacation rentals offer more space and privacy compared to hotels. You'll also have access to a kitchen, allowing you to prepare your own meals and save on dining costs. Many rentals also have unique features, like private pools or balconies with stunning views.
  • What are the top sports attractions and facilities in Sarasota, FL?

    Sarasota is a great place for sports enthusiasts. The Ed Smith Stadium is home to the Baltimore Orioles spring training, attracting baseball fans from all over. The Sarasota Polo Club offers exciting polo matches, and the Sarasota Sailing Squadron hosts various sailing events throughout the year.

Destinations nearby

Best Sarasota, FL holiday rentals with a balcony

Harbor Towers 1 Bedroom Pool View - Sarasota, FL
9.7 90 reviews
Sarasota, FL
01/07 – 30/09
152 â‚¬/nighttotal: 13832 â‚¬ (91 )

Harbor Towers 1 Bedroom Pool View

1 2
house , Siesta Key
This Siesta Key house is a 7-minute walk from Crescent Beach and less than a mile from Siesta Key Beach, putting you right in the heart of the action. The property has received excellent ratings for location, cleanliness, and overall experience.
The house features a comfortable living space, a fully equipped kitchen, and a bathroom with a hairdryer. You can enjoy the on-site swimming pool, tennis court, and fitness centre, or relax on the terrace with a view of the pool.
Annie's Escape - 5 Mins To Downtown - Hottub - Sarasota, FL
10 7 reviews
Sarasota, FL
11/08 – 19/08
141 â‚¬/nighttotal: 1128 â‚¬ (8 )

Annie's Escape - 5 Mins To Downtown - Hottub

3 2
house , Sarasota
This Sarasota holiday home is conveniently located near downtown, 9.5km from the Ringling Museum of Art and 9km from Sarasota Bradenton International Airport.
The 93 square metre property boasts three bedrooms, two bathrooms, sleeps eleven guests, and features a fully equipped kitchen, private hot tub, spa, garden, terrace, free Wi-Fi and parking.
Gertrude Siesta | Budget Friendly, Private Patio, 5-min To Beach, 1-min To Dining & Entertainment! - Sarasota, FL
Sarasota, FL
02/07 – 05/07
1316 â‚¬/nighttotal: 3948 â‚¬ (3 )

Gertrude Siesta | Budget Friendly, Private Patio, 5-min To Beach, 1-min To Dining & Entertainment!

3 9
apartment , Siesta Key
This Siesta Key apartment, situated less than 1.6km from Crescent Beach and Siesta Key Beach and around 3.2km from Turtle Beach, offers convenient access to Siesta Key's stunning coastline.
Sleeping up to 12 guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, free Wi-Fi, a swimming pool, on-site water park, and a terrace, making it ideal for families or large groups seeking a self-catering holiday rental near the beach.
2br/1ba Sienna Park Apartment - Sarasota, FL
9.4 43 reviews
Sarasota, FL
09/07 – 12/07
189 â‚¬/nighttotal: 567 â‚¬ (3 )

2br/1ba Sienna Park Apartment

2 2
apartment , Gulf Gate Estates
This two-bedroom apartment is situated in Sarasota, just 11 miles from The John and Mable Ringling Museum of Art and Sarasota Bradenton International Airport, offering a convenient location for exploring the area. The property has received excellent ratings for user experience, location, and cleanliness.
The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, a private balcony with pool views, and a barbecue area. Enjoy access to a swimming pool, a tennis court, and a garden, along with free Wi-Fi and private parking.

Best Sarasota, FL holiday rentals with parking

4-bedroom Dog-friendly Home, Just 13 Miles From Siesta Key Beach! Private Pool - Sarasota, FL
10 125 reviews
Sarasota, FL
13/07 – 17/07
529 â‚¬/nighttotal: 2116 â‚¬ (4 )

4-bedroom Dog-friendly Home, Just 13 Miles From Siesta Key Beach! Private Pool

4 11
apartment , North Sarasota
This spacious four-bedroom house in North Sarasota is located approximately 2.6 kilometres from University Park Country Club and within a 9.7 kilometre radius of Sarasota Jungle Gardens and the Mall at University Town Centre.
The 199 square metre property boasts a family-friendly layout sleeping up to 13 guests, featuring a private pool, fully equipped kitchen, free Wi-Fi, and outdoor amenities including a garden and barbecue grills.
Central City Condominiums #203 2br/2ba - Sarasota, FL
10 4 reviews
Sarasota, FL
09/08 – 14/08
124 â‚¬/nighttotal: 620 â‚¬ (5 )

Central City Condominiums #203 2br/2ba

2 3
apartment , Sarasota
This Sarasota flat is situated in the Arlington Park district, offering convenient access to St. Armands Circle (approximately 6 kilometres away), The Mall at University Town Center (around 8 kilometres away), Siesta Key Public Beach (about 7 kilometres away), and LECOM Park.
This two-bedroom, two-bathroom apartment accommodates up to six guests and includes essential amenities such as Wi-Fi, air conditioning, a dryer, towels, basic toiletries, and a hairdryer.
Poppie’s House - Sarasota, FL
Sarasota, FL
10/07 – 12/07
281 â‚¬/nighttotal: 562 â‚¬ (2 )

Poppie’s House

3 4
apartment , Sarasota
This newly built 2025 flat in Sarasota's Arlington Park district is situated on a quiet cul-de-sac, a short 5-kilometre drive from Downtown Sarasota, 10 kilometres from Siesta Key Beach, and 7 kilometres from St. Armands Circle.
The family-friendly accommodation sleeps six guests across three bedrooms and two bathrooms, featuring air conditioning, Wi-Fi, a fully equipped kitchen with a fridge, microwave, and dishwasher, a garden, parking, and provided beach essentials.
The Village Breeze 8br With Heated Pool, Near Beach, 250ft To Siesta Key Village! - Sarasota, FL
Sarasota, FL
30/08 – 06/09
2025 â‚¬/nighttotal: 14175 â‚¬ (7 )

The Village Breeze 8br With Heated Pool, Near Beach, 250ft To Siesta Key Village!

8 20
apartment , Siesta Key
This eight-bedroom Siesta Key apartment is situated in Siesta Key Village, a six-minute walk (approximately 0.4 km) from Siesta Key Beach and 76 metres from the Village centre.
Sleeping up to 34 guests, this self-catering property boasts a heated pool, water park, children's playground, free Wi-Fi, and is equipped for disabled guests.
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