Holiday Rentals in Sarasota, FL

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Sarasota, FL holiday rentals
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Best Holiday rentals and Airbnb offers 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

Centrally Located Renovated Sarasota Retro Retreat - Sarasota, FL
10 88 reviews
Sarasota, FL
12/10 – 15/10
SG$314/nighttotal: SG$942 (3 )

Centrally Located Renovated Sarasota Retro Retreat

1 4
apartment , Sarasota
This Sarasota duplex, near Gillespie Park and a 24km drive from Siesta and Lido Key beaches and the University Town Center (UTC) Mall, offers a convenient location for exploring the city.
The impeccably renovated two-bedroom, one-bathroom property sleeps four, features a well-equipped kitchenette, private patio, complimentary beach gear, and organic cleaning products; nearby activities include cornhole and a fire pit.
Escape To Vitamin Sea: Private Pool, Guest Suite, Minutes To Sarasota's Parks, Downtown And Beaches! - Sarasota, FL
9.4 59 reviews
Sarasota, FL
01/12 – 30/04
SG$534/nighttotal: SG$80100 (150 )

Escape To Vitamin Sea: Private Pool, Guest Suite, Minutes To Sarasota's Parks, Downtown And Beaches!

4 2
apartment , Sarasota
This Sarasota holiday home is centrally located, within 1.6 to 3.2km of Sarasota Commons, Tuttle Avenue Park, Northeast Plaza, Colonial Village Shopping Centre, and the Bobby Jones Golf Complex.
The 140 square metre property boasts four bedrooms, three bathrooms, sleeps eight guests, and features a private pool, fully equipped kitchen, BBQ grills, and cable TV.
2 Miles To #1 Beach Siesta Key - Sarasota, FL
9.9 288 reviews
Sarasota, FL
19/12 – 20/02
SG$250/nighttotal: SG$15750 (63 )

2 Miles To #1 Beach Siesta Key

2 2
apartment , Gulf Gate Estates
This house is located in Gulf Gate Estates, just 5km from Siesta Key Beach and close to Gulf Gate Mall, offering a convenient and peaceful stay. The property has excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable experience.
The house has 2 bedrooms and 1 bathroom, covering 130 square metres and accommodating up to 4 guests. Enjoy amenities like a Jacuzzi, a garden, and a terrace, as well as a fully equipped kitchen and BBQ facilities for an enjoyable stay.
Charming 3-bedroom House On Legacy Trail W/swimspa - Sarasota, FL
9.8 25 reviews
Sarasota, FL
22/07 – 29/07
SG$216/nighttotal: SG$1512 (7 )

Charming 3-bedroom House On Legacy Trail W/swimspa

1 5
apartment , Sarasota
This Sarasota cottage, ideally located within a 1.6km walk of Payne Park and a trolley stop for beach access, offers easy access to Publix supermarket and the Legacy Trail via a private gate.
The three-bedroom, two-bathroom property sleeps six guests and boasts a private fenced yard with a heated swim spa, a mid-century modern interior, high-end kitchen appliances including a Breville Nespresso machine, and childproofing features.

Best Sarasota, FL holiday rentals with a pool

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

Spacious Home With Heated Pool 3 Miles From Img! - Sarasota, FL
Sarasota, FL
02/07 – 05/07
SG$664/nighttotal: SG$1992 (3 )

Spacious Home With Heated Pool 3 Miles From Img!

4 9
house , Bayshore Gardens
This Bayshore Gardens property is conveniently located near IMG Academy (4.8km), Greens of Manatee Golf Club (6.6km), and Sarasota Bradenton International Airport (5km), offering easy access to various attractions.
This four-bedroom, two-bathroom house boasts 172 square metres of floor space, comfortably accommodating up to 21 guests with amenities including a heated swimming pool, free Wi-Fi, and private parking.
Welcome To Shoreline: 4br, Heated Pool, 7miles To Gulf Beaches. - Sarasota, FL
10 16 reviews
Sarasota, FL
27/06 – 04/07
SG$630/nighttotal: SG$4410 (7 )

Welcome To Shoreline: 4br, Heated Pool, 7miles To Gulf Beaches.

4 7
apartment , Sarasota
This four-bedroom apartment is situated in the Bellevue Terrace neighbourhood of Sarasota, just 13 kilometres from Siesta Key Beach and a short walk from Pinecraft. The property offers a private garden, a heated pool, a tennis court, and parking for guests, making it ideal for families or groups of up to 11 people.
Kingston Arms 1st Fl Cottage - Sarasota, FL
Sarasota, FL
08/07 – 17/07
SG$358/nighttotal: SG$3222 (9 )

Kingston Arms 1st Fl Cottage

1 3
house , Sarasota
Kingston Arms 1st Fl Cottage is a Sarasota self-catering property situated 2.6km from Mote Marine Laboratory, offering convenient access to Lido Beach, South Lido Beach, St. Armands Circle, and attractions including the John and Mable Ringling Museum of Art (9.7km).
This one-bedroom cottage, sleeping up to nine guests and boasting two bathrooms, features a fully equipped kitchen with dishwasher, free Wi-Fi, private parking, a swimming pool, air conditioning, satellite TV, and elevator access; guests must be 25 or older.
Free Htd Pool  Steps To The Bay  Pet-friendly  Near Siesta Key - Sarasota, FL
9.8 148 reviews
Sarasota, FL
30/07 – 02/08
SG$854/nighttotal: SG$2562 (3 )

Free Htd Pool Steps To The Bay Pet-friendly Near Siesta Key

4 10
apartment , Whitfield
This four-bedroom apartment is located in Sarasota, just one kilometre from the bay and within a short drive of popular beaches like Lido Key, Longboat Key, Anna Maria Island, and Siesta Key. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment spans 195 square metres and can comfortably accommodate up to 13 guests. It features a fully equipped kitchen, a spacious living area, a private garden, a terrace, a swimming pool, and a range of amenities for families, including a gaming station and a treehouse.

Frequently asked questions about holiday rentals in Sarasota, FL

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

    For families, there's the Mote Marine Laboratory and Aquarium, which is always a hit. And of course, there's the Sarasota Jungle Gardens, where you can see all sorts of exotic animals. For a fun day out, head to the Sarasota County Fairgrounds, which hosts events throughout the year.
  • What are the best Airbnb and vacation rentals 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 get better rates and less crowds compared to the peak season, which is from December to April.
  • What are the most popular Airbnbs in Sarasota, FL?

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

    Sarasota has a lot of fun events! The Sarasota Film Festival is a big one, held in April. In March, there's the Suncoast Music Festival, which is a great music festival. If you're here in October, check out the Sarasota Chalk Festival, it's a real unique event.
  • What are the best vacation rentals with a pool in Sarasota, FL?

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

    For a budget-friendly day out, head to the Bayfront Park, which has beautiful views of the bay. You can also take a stroll along the Legacy Trail, which is a scenic paved trail that runs through the city. And for a free cultural experience, visit the Sarasota Opera House.
  • What are the best rentals for families and kids in Sarasota, FL?

  • What are the best restaurants with local dishes in Sarasota, FL?

    For local dishes, you can't go wrong with the seafood. I recommend checking out the restaurants on St. Armands Circle, like the Columbia Restaurant, which is known for its Spanish and Cuban cuisine. For a more casual option, try the Lazy Lobster, which is a popular spot for fresh seafood.
  • What are the best rentals or Airbnbs with a jacuzzi in Sarasota, FL?

  • What are the best walking or cycling routes in Sarasota, FL?

    The Legacy Trail is a great option for walking or cycling, it runs for 12 miles along the old railway line. If you want a beach walk, try the Siesta Key Beach, which is known for its soft, white sand. For a more scenic route, head to the Myakka River State Park, which has several hiking trails and a beautiful river.
  • Are there pet-friendly attractions in Sarasota, FL?

    Yes, there are lots of pet-friendly attractions in Sarasota! You can take your dog to the beach, just make sure to keep them on a leash. There are also several dog parks in the city, like the Celery Fields Dog Park. And for a fun day out, head to the Sarasota Farmers Market, which is pet-friendly.
  • What are the benefits of choosing a vacation rental in Sarasota, FL?

    Vacation rentals offer a lot of flexibility and privacy. They're often more spacious than hotel rooms, and you can cook your own meals, which can save money. And if you're travelling with a group or family, it can be a more convenient option.

Destinations nearby

Best Sarasota, FL holiday rentals with a balcony

Beautiful Updated 2bedroom Suite Minutes To Downtown, Amazing Beaches, Restaurants, Theaters And More - Sarasota, FL
9.3 43 reviews
Sarasota, FL
01/07 – 05/07
SG$379/nighttotal: SG$1516 (4 )

Beautiful Updated 2bedroom Suite Minutes To Downtown, Amazing Beaches, Restaurants, Theaters And More

2 2
apartment , Sarasota
This Sarasota apartment offers a central location, minutes from downtown, Sarasota's beaches, and within a 2.1 km radius of the Ringling Museum of Art and 2.1 km from Indian Beach.
The 79 square metre self-catering property features two bedrooms, one bathroom, sleeps seven guests, and includes a terrace, garden access, free Wi-Fi, private parking, and a tennis court.
100 Percent Private, Tiki-bar, 250steps To Beach And Village! - Sarasota, FL
Sarasota, FL
13/07 – 17/07
SG$2001/nighttotal: SG$8004 (4 )

100 Percent Private, Tiki-bar, 250steps To Beach And Village!

6 11
house , Siesta Key
This Siesta Key holiday home is a seven-minute walk from Siesta Key Beach, 1.9 kilometres from Crescent Beach, and within 10-18 kilometres of various Sarasota attractions.
This six-bedroom property boasts a 2787 square metre floor area, four bathrooms, a private Tiki bar, and can comfortably accommodate 43 guests, offering easy beach access and free Wi-Fi.
Kingston Arms, 2nd Floor, Walk To Beach - Sarasota, FL
9.8 82 reviews
Sarasota, FL
11/08 – 19/08
SG$349/nighttotal: SG$2792 (8 )

Kingston Arms, 2nd Floor, Walk To Beach

2 2
house , Sarasota
Kingston Arms is a short walk from Lido Beach in Sarasota, close to South Lido Beach and Longboat Key Beach, offering easy access to the beautiful white sand and turquoise waters. This property has been rated excellent for location, cleanliness, and user experience.
This house is 96 square metres and features an elevator, free private parking, and complimentary Wi-Fi. Enjoy a comfortable stay with air conditioning, a seating area, a fully equipped kitchen, satellite TV, and a bathroom with a hairdryer, as well as a swimming pool, jacuzzi, terrace, garden, and a location close to the St. Armands Circle shopping and dining district.
Tiny House Green Lifeguard Stand - Sleeps 5 - Sarasota, FL
9.5 148 reviews
Sarasota, FL
25/06 – 27/06
SG$269/nighttotal: SG$538 (2 )

Tiny House Green Lifeguard Stand - Sleeps 5

2 2
apartment , Gulf Gate Estates
This house is located in Gulf Gate Estates, just under 2 kilometres from Gulf Gate Mall and Crescent Beach, and 2.4 kilometres from Siesta Key Beach. It has received excellent ratings for its location, cleanliness, and overall experience.
The house has two bedrooms and one bathroom, suitable for up to five guests. It offers modern amenities such as air conditioning, a fully equipped kitchen, a garden, parking, and Wi-Fi, as well as a patio with barbecue grills.

Best Sarasota, FL holiday rentals with parking

Cozy Studio Only 10 Minutes By Car Of Siesta Key - Sarasota, FL
8.6 23 reviews
Sarasota, FL
26/06 – 28/06
SG$155/nighttotal: SG$310 (2 )

Cozy Studio Only 10 Minutes By Car Of Siesta Key

1 2
studio , South Gate Ridge
Apartment listing with an excellent rating of 86% based on 23 reviews. You will be located in South Gate Ridge.
Services and facilities include a barbecue, air conditioning and a fridge. Take advantage of the Free Parking with this accommodation.
Poppie’s House - Sarasota, FL
Sarasota, FL
10/07 – 12/07
SG$417/nighttotal: SG$834 (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 Strand Of Sarasota 509 - Sarasota, FL
10 20 reviews
Sarasota, FL
27/06 – 05/07
SG$329/nighttotal: SG$2632 (8 )

The Strand Of Sarasota 509

2 3
apartment , Sarasota
This Sarasota waterfront condo, situated in Central Sarasota, offers easy access to St Armands Circle, Lido Beach, and Siesta Key Beach.
The two-bedroom, two-bathroom apartment sleeps four, boasting a private balcony, swimming pool, jacuzzi, and direct Gulf access with private boat slips; on-site amenities include a spa, sauna, and kayak/paddleboard launch.
4br Sleeps 12 | Game Room | Near Beaches 4 Groups - Sarasota, FL
Sarasota, FL
02/07 – 05/07
SG$690/nighttotal: SG$2070 (3 )

4br Sleeps 12 | Game Room | Near Beaches 4 Groups

4 9
apartment , North Sarasota
This waterfront holiday flat in North Sarasota offers convenient access to lake walks, is an 11-minute drive (approximately 17.7 kilometres) to The Mall at University Town Centre, and a 12-minute drive (approximately 19.3 kilometres) to Premier Sports Campus at Lakewood Ranch.
This 4-bedroom, 2-bathroom holiday home accommodates up to 12 guests and features on-site parking, a garden, a balcony, complimentary Wi-Fi, air conditioning, a fully equipped kitchen with a washer and dryer, and a workspace.
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