Holiday Rentals in Sarasota

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Sarasota holiday rentals
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Best Holiday rentals and Airbnb offers in Sarasota

Search Coastal Holiday Rentals near Sarasota

Experience relaxing coastal vibes at seaside holiday rentals in Sarasota, positioned short distances from local beach-town shorelines.

Lido Beach/st. Armands Condo - Sarasota
9.9 28 reviews

Lido Beach/st. Armands Condo

apartment, Sarasota
This Sarasota beachfront apartment, a short 0.5km stroll from St. Armands Circle and Lido Beach, offers easy access to shops, restaurants, and the Sarasota-Bradenton International Airport (a 10-minute, 8km drive).
The two-bedroom, two-bathroom condo sleeps four, boasting a fully equipped kitchen, washer-dryer, screened porch, community pool, Jacuzzi, and parking; beach chairs and umbrella are provided for guest use.
2br Beach Style W Pool Beach Club Siesta 204c Rva - Sarasota
9.0 95 reviews

2br Beach Style W Pool Beach Club Siesta 204c Rva

apartment, Siesta Key
The Beach Club At Siesta Key #204c Resort By Rva is a two-bedroom apartment located on Siesta Key, just a short distance from Crescent Beach and Siesta Key Beach, making it ideal for enjoying the beautiful white sand and calm waters. This accommodation has received excellent user and location ratings, and a very good cleanliness rating.
The apartment has two bedrooms and two bathrooms, accommodating up to six guests. Enjoy a comfortable stay with amenities including a swimming pool, Jacuzzi, tennis court, and a terrace or balcony, perfect for relaxing and enjoying the beautiful surroundings.
Walk To The Beach! Luxury 4 Br 5 Ba Retreat On Siesta Key On Grand Canal Near Village - Sarasota
10 1 review

Walk To The Beach! Luxury 4 Br 5 Ba Retreat On Siesta Key On Grand Canal Near Village

house, Siesta Key
This canal-front luxury townhouse in Siesta Key is situated just 320 metres from Siesta Key Beach, offering exclusive access to the Grand Canal for boating and watersports.
This four-bedroom residence spans 285 square metres, accommodates up to 12 guests, and features a private elevator, heated pool and spa, and multiple terraces with tropical vistas, including a panoramic view of Siesta Key Beach.
The Palm Bay Club Siesta Key Beach - Sarasota
9.7 140 reviews

The Palm Bay Club Siesta Key Beach

apartment, Siesta Key
This Siesta Key apartment, situated less than 1.6km from Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offers convenient access to local attractions including St. Boniface Episcopal Church Labyrinth.
The two-bedroom, two-bathroom property sleeps four guests and boasts a fully equipped kitchen, private patio, free Wi-Fi, swimming pool, Jacuzzi, fitness centre and parking, ensuring a comfortable and convenient stay.

Best family friendly Sarasota holiday rentals

Among the 4506 accommodations in Sarasota, here are the 4 best family friendly rentals

Upstairs 4/2 In Srq (No Clean Fee W/12pm Checkout) - Sarasota
10 107 reviews

Upstairs 4/2 In Srq (No Clean Fee W/12pm Checkout)

apartment, Sarasota Springs
This spacious Sarasota Springs duplex, situated approximately 13km from Siesta Key Beach and within a 20-minute drive of Nathan Benderson Park and the University Town Center mall, offers convenient access to local attractions.
The four-bedroom, two-bathroom property sleeps eight guests and includes a fully equipped kitchen, multiple TVs, games consoles, a shared laundry room, and a fenced yard; enjoy added privacy and security.
126 M² House ∙ 3 Bedrooms ∙ 8 Guests - Sarasota
10 2 reviews

126 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Sarasota
City Cottage, a 1920s bungalow in Sarasota's Gillespie Park neighbourhood, is located half a kilometre from downtown Sarasota and a short drive from Lido Beach and St Armands Circle.
This three-bedroom, two-bathroom property offers 126 square metres of living space, sleeping eight guests comfortably with amenities including a private heated pool, free Wi-Fi, and a fully equipped kitchen; nearby attractions include boutique shops, restaurants and the arts scene.
Paradise Heated Pool Home Near Img And Siesta Key Beach - Sarasota
9.5 69 reviews

Paradise Heated Pool Home Near Img And Siesta Key Beach

house, Samoset
This Samoset house is conveniently located in a quiet neighbourhood, just 6.7 miles from the John and Mable Ringling Museum of Art and 5 miles from Sarasota Bradenton International Airport. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This 3-bedroom property provides a spacious and comfortable space for families and groups. It features a private pool, a fully equipped kitchen, a patio, and a garden, along with amenities like a jacuzzi, a tennis court, and a spa.
Perfect Florida Location: Craftsman Carriage House - Sarasota
9.8 166 reviews

Perfect Florida Location: Craftsman Carriage House

house, Sarasota
This newly built Sarasota Craftsman-style carriage house, located in downtown Sarasota, offers convenient access to Sarasota's beaches, golf courses, and cultural attractions.
The one-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen with modern appliances, a private porch, dedicated parking, and all utilities included; a shared gas grill is available for outdoor cooking.

Frequently asked questions about holiday rentals in Sarasota

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

    You definitely want to visit the Ringling Museum, it's a real gem! It's a beautiful complex with art, circus history, and a stunning mansion. And don't miss out on the beautiful beaches, Siesta Key Beach is a must-see, it's known for its soft white sand.
  • What are the best Airbnb and holiday rentals in Sarasota?

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

    For a central location, downtown Sarasota is a great choice, you're within walking distance of shops, restaurants, and the waterfront. If you prefer a more relaxed atmosphere, Siesta Key is a great option, it's known for its beautiful beaches and laid-back vibe.
  • What are the most popular Airbnbs in Sarasota?

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

    The Mote Marine Laboratory & Aquarium is a great option for families, it's home to a variety of marine life. The Sarasota Jungle Gardens is also a fun place to visit, with exotic animals and lush gardens. And don't forget about the beaches, they're perfect for building sandcastles and splashing in the waves.
  • What are the best holiday rentals with a pool in Sarasota?

  • 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 avoid the peak season crowds and enjoy more affordable prices.
  • What are the best rentals for families and kids in Sarasota?

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

    The Sarasota Film Festival is a big event in the spring, showcasing independent films. The Suncoast Food & Wine Festival is another popular event, with food and drink from local vendors. And the annual Sarasota Chalk Festival is a must-see, with artists creating stunning chalk masterpieces on the streets.
  • What are the best rentals or Airbnbs with a jacuzzi in Sarasota?

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

    Take a stroll along the Bayfront, it's a great way to enjoy the scenery and get some exercise. You can also visit the Selby Gardens, a beautiful botanical garden with a variety of plants and flowers. And don't forget about the beaches, they're free and a great way to relax and enjoy the sunshine.
  • What are the best restaurants with local dishes in Sarasota, FL?

    For fresh seafood, try The Old Salty Dog, it's a local favourite. If you're looking for something a bit more upscale, try The Capital Grille, they have a great selection of steaks and seafood. And for a taste of the local culture, visit the Sarasota Farmers Market, you'll find a variety of local vendors selling fresh produce, baked goods, and more.
  • What are the best walking or cycling routes in Sarasota, FL?

    The Legacy Trail is a great option for both walking and cycling, it stretches for 12.5 km along the former route of the Seaboard Air Line Railway. For a more scenic route, try the Bayfront Trail, it offers beautiful views of the water and the downtown area.
  • Are there pet-friendly attractions in Sarasota, FL?

    Yes, many beaches in Sarasota are dog-friendly, including Siesta Key Beach and Lido Beach. You can also find plenty of dog-friendly restaurants and cafes. And don't forget about the dog park at the Nathan Benderson Park, it's a great place for your furry friend to run and play.
  • What are the benefits of choosing a vacation rental in Sarasota, FL?

    Vacation rentals offer more space and privacy compared to hotels. They are often more affordable, especially for larger groups. And many offer amenities like kitchens and laundry facilities, which can be very convenient for families.
  • What are the top sports attractions and facilities in Sarasota, FL?

    The Nathan Benderson Park is a major sports complex, hosting events like rowing competitions and triathlons. The Sarasota Polo Club is also a popular attraction, with matches held throughout the year. And of course, you can always enjoy a game of tennis or pickleball at one of the many public courts around town.

Popular destinations

Find the Best Holiday Rentals with a Pool in Sarasota

Our holiday rentals near the water in Sarasota include a pool, so a relaxing swim is always on the cards.

City Cottage | Heated Cocktail Pool, Tiki Bar & Walk To City Of Sarasota - Sarasota
9.2 9 reviews

City Cottage | Heated Cocktail Pool, Tiki Bar & Walk To City Of Sarasota

apartment, Sarasota
City Cottage, a Sarasota bungalow, is located 0.8km from downtown Sarasota, offering easy access to Lido Beach and St Armands Circle via the free trolley.
This three-bedroom, two-bathroom holiday home boasts 126 square metres of space, sleeping up to eight guests and featuring a private heated pool, a tiki bar, and essential amenities including a fully equipped kitchen and free Wi-Fi.
Cozy Bungalow With Shared Pool,  Internet, Onsite Washer And Dryer - Sarasota
No reviews

Cozy Bungalow With Shared Pool, Internet, Onsite Washer And Dryer

apartment, Sarasota
This pet-friendly apartment in Sarasota's Bayou Oaks district is a 10-minute walk from Sarasota Jungle Gardens and a 3-minute drive from the John and Mable Ringling Museum of Art.
This 102-square-metre holiday let offers three bedrooms, two bathrooms, and accommodates six guests with air conditioning, Wi-Fi, a kitchen featuring an oven and microwave, and access to a shared swimming pool and balcony with barbecue facilities.
Charlotte Ave Coastal Retreat Private Pool Fire Pit & Backyard Lounge - Sarasota
No reviews

Charlotte Ave Coastal Retreat Private Pool Fire Pit & Backyard Lounge

apartment, Sarasota
This pet-friendly holiday flat in Sarasota's Bellevue Terrace district offers sea views and is a 5-minute drive to Marie Selby Botanical Gardens and a 6-minute drive to Marina Jack.
This 111 square meter residence, accommodating up to six guests, features three bedrooms, two bathrooms, a full kitchen with an oven and stovetop, air conditioning, a balcony, and on-site bicycle rentals.
Sarasota Sands Retreat/pool - Sarasota
9.6 14 reviews

Sarasota Sands Retreat/pool

apartment, Sarasota
This detached house in Sarasota offers proximity to Siesta Key Beach and Lido Key, located just a short drive from downtown Sarasota, St. Armands Circle, and direct access to the Legacy Trail for cycling and walking.
This four-bedroom residence accommodates up to eight guests and features a private heated swimming pool with spa jets, a fully equipped kitchen, an outdoor dining area, and an in-home washer and dryer, with free on-site parking provided.

Our Favourite Holiday Rentals with Parking in Sarasota

Parking is sorted from the start as these holiday rentals near the water in Sarasota include free on-site spaces.

3 Bedroom House North End Of Siesta Key - Short Walk To Shell Beach - Sarasota
9.7 34 reviews

3 Bedroom House North End Of Siesta Key - Short Walk To Shell Beach

apartment, Sarasota
This charming cottage is situated on the North End of Siesta Key, just a short drive from Southside Village, Downtown Sarasota, and St. Armand's Circle, offering easy access to the area's attractions. The accommodation has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage spans 151 square metres and comfortably accommodates up to six guests across its three bedrooms and three bathrooms. The fully equipped kitchen, air conditioning, private garden, and screened lanai with a charming banyan tree provide a relaxing and comfortable stay.
Sleeps 8 Pool Dog Friendly 6 Miles To Beach - Sarasota
No reviews

Sleeps 8 Pool Dog Friendly 6 Miles To Beach

house, Sarasota
This Sarasota villa is located 800 metres from the Ringling Museum and a 16-minute walk from Indian Beach.
This dog-friendly property offers 210 square metres of living space, air conditioning, free WiFi, parking, a private swimming pool, and accommodates up to 8 guests.
72 M² House ∙ 2 Bedrooms ∙ 6 Guests - Sarasota
No reviews

72 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Sarasota
Holiday house rental for 6 guests. You will be in Sarasota.
Facilities and services: free parking, a washing machine and a fridge. Take advantage of the garden in this house!
2 Villas Back To Back, 2 Private Heated Pools, New - Sarasota
10 9 reviews

2 Villas Back To Back, 2 Private Heated Pools, New

apartment, South Sarasota
Luna Flores, a renovated property in South Sarasota, offers a six-bedroom, four-bathroom apartment conveniently located near Siesta Key's beaches and attractions, though precise distances aren't specified.
This South Sarasota dwelling sleeps up to 16 guests and boasts two heated swimming pools, a fully renovated kitchen, and high-quality linens; further details regarding the property's size and specific distances to landmarks are unavailable.

Discover 5-Star Self-Catering Rentals in Sarasota

There is much to be said for a well-chosen luxury holiday rental or Airbnb in Sarasota, offering wonderful rooms and a location worth the trip. Choose from the best offers.

The Cottage, Very Close To Siesta Beach! - Sarasota
9.7 425 reviews

The Cottage, Very Close To Siesta Beach!

house, Sarasota

Best Sarasota holiday rentals with a balcony

3606 Villa Franca - Pet Friendly - Sarasota
8.8 51 reviews

3606 Villa Franca - Pet Friendly

house, Southgate
Spacious 2br Retreat W/large Spool Near Downtown - Sarasota
No reviews

Spacious 2br Retreat W/large Spool Near Downtown

apartment, Sarasota
Walk To Siesta Key Beach - Family & Pet Friendly - Private Saltwater Pool - Fenced Yard -Gourmet Wolf Subzero Kitchen -Garage -Close To Restaurants Shops-aylees Private Beach House - Sarasota
No reviews

Walk To Siesta Key Beach - Family & Pet Friendly - Private Saltwater Pool - Fenced Yard -Gourmet Wolf Subzero Kitchen -Garage -Close To Restaurants Shops-aylees Private Beach House

house, Siesta Key
Relaxing Getaway Near Downton Sarasota, Lido Key & Siesta Beach - Sarasota
10 10 reviews

Relaxing Getaway Near Downton Sarasota, Lido Key & Siesta Beach

apartment, Sarasota

Best Pet-Friendly Holiday Rentals in Sarasota

Dog-friendly holiday rentals in Sarasota feature outdoor showers and easy access to pet-welcoming beaches.

Chic Downtown Gem - The Coconut Hut - Sarasota
10 14 reviews

Chic Downtown Gem - The Coconut Hut

apartment, Sarasota
Colorful Waterfront Cabin Rentals On The Braden River Near Sarasota, Florida - Sarasota
10 1 review

Colorful Waterfront Cabin Rentals On The Braden River Near Sarasota, Florida

cabin, North Sarasota
Casa Azul 3bedroom - Sarasota
9.8 319 reviews

Casa Azul 3bedroom

apartment, Sarasota
Gertrude's Siesta | 8-steps To Beach Path! 4-min Dining & Music! Low Price - Sarasota
9.6 76 reviews

Gertrude's Siesta | 8-steps To Beach Path! 4-min Dining & Music! Low Price

apartment, Siesta Key

Search Holiday Rentals with a Hot Tub in Sarasota

A holiday rental or Airbnb with a hot tub near the water in Sarasota is ideal for a private evening soak.

Home With Fenced Yard, Hot Tub, Grill And 3 King Beds! - Sarasota
No reviews

Home With Fenced Yard, Hot Tub, Grill And 3 King Beds!

house, Southgate
Private Hot Tub + Fire Pit 15 Min To Lido Beach - Sarasota
10 8 reviews

Private Hot Tub + Fire Pit 15 Min To Lido Beach

apartment, Sarasota
Sarasota Bay Views Luxury Waterfront - Sarasota
10 6 reviews

Sarasota Bay Views Luxury Waterfront

apartment, Sarasota
Gertrude's Siesta | Pool, Jacuzzi! 1-minute To Beach! 4-min Dining & Music! - Sarasota
10 13 reviews

Gertrude's Siesta | Pool, Jacuzzi! 1-minute To Beach! 4-min Dining & Music!

apartment, Siesta Key

Top-Rated Holiday Rentals with a Spa in Sarasota

After enjoying everything Sarasota has to offer, a spa session at your holiday rental is the ideal way to finish the day.

Sarasota Coastal Cottage - Sarasota
9.9 60 reviews

Sarasota Coastal Cottage

apartment, Sarasota
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