Siesta Key, FL Short term rentals

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Siesta Key, FL short term rentals
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Best Short term and Weekly rentals in Siesta Key, FL

Best Siesta Key, FL short term rentals with a balcony

Two-level, Heated Pool, Trolley To Beach & Village - Siesta Key, FL
9.7 3 reviews
Siesta Key, FL
18/07 – 25/07
£206/nighttotal: £1442 (7 )

Two-level, Heated Pool, Trolley To Beach & Village

2 2
apartment , Siesta Key
This Siesta Key apartment, a short walk from Crescent Beach and a 2.1km drive from Siesta Key Beach, offers easy access to the island's main attractions.
The 124 square metre, two-level property sleeps up to 11 guests and boasts three bathrooms, a fully equipped kitchen, private parking, a swimming pool, and a terrace; free Wi-Fi is also provided.
Condo# 414 2 Bed/2 Bath Condo Steps To Siesta Key Beach! - Siesta Key, FL
10 2 reviews
Siesta Key, FL
01/08 – 08/08
£242/nighttotal: £1694 (7 )

Condo# 414 2 Bed/2 Bath Condo Steps To Siesta Key Beach!

2 5
apartment , Siesta Key
This Siesta Key apartment is located steps from Siesta Key Beach, consistently ranked among the world's best, and a short walk from Siesta Village's restaurants and shops.
The 100-square-metre (1076 square feet) property, a top-floor end unit, sleeps six comfortably in two bedrooms and two bathrooms, boasting a fully equipped kitchen, screened lanai, multiple TVs, and access to a swimming pool, fitness centre, and tennis court.
Unwind In Style At Bay Oaks E-93: Tennis Court And Shared Pool Near Beach - Siesta Key, FL
9.4 3 reviews
Siesta Key, FL
30/07 – 09/08
£237/nighttotal: £2370 (10 )

Unwind In Style At Bay Oaks E-93: Tennis Court And Shared Pool Near Beach

2 5
apartment , Siesta Key
This Siesta Key apartment is situated a short walk from Siesta Key Beach and Crescent Beach, with Turtle Beach 4.5km away.
The 102-square-metre property boasts three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private balcony, in-unit laundry, and access to a swimming pool, spa, and tennis court.
Aqua Oasis- Tiny House Sleeps 4 & Pet Friendly - Siesta Key, FL
9.0 103 reviews
Siesta Key, FL
25/06 – 01/07
£131/nighttotal: £786 (6 )

Aqua Oasis- Tiny House Sleeps 4 & Pet Friendly

2 4
apartment , Gulf Gate Estates
This house is located in Sarasota, just 2 kilometres from Gulf Gate Mall and 3 kilometres from Crescent Beach, with Siesta Key Beach a little further away. It enjoys a quiet residential setting, making it a relaxing escape from the city. This property has received very good user ratings, with excellent location and cleanliness scores.
The house has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. It features a fully equipped kitchen, air conditioning, a garden, parking, and internet access, ensuring a comfortable and enjoyable stay.

Guest-Favourite Family-Friendly Holiday Lets in Siesta Key, FL

Travelling to Siesta Key, FL with children? A family-friendly short-term let makes everything easier, with accessible beaches.

Come To The Sea And Stay On The Key! - Siesta Key, FL
9.5 235 reviews
Siesta Key, FL
17/07 – 24/07
£174/nighttotal: £1218 (7 )

Come To The Sea And Stay On The Key!

1 2
apartment , Siesta Key
This one-bedroom apartment is located just across the street from Siesta Key Beach, one of the best beaches in the USA, and is just a short walk from the intercoastal waterway. The apartment has excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment offers a comfortable living space for up to 4 guests and includes a well-equipped kitchen with a fridge, freezer, and microwave oven. Guests can enjoy a private patio, access to a swimming pool, a garden, and parking. The apartment also provides beach amenities such as chairs, an umbrella, a cooler, and sand toys.
Bayside Escape | Water Views, Walk To Siesta Key Beach, Balcony & Community Pool - Siesta Key, FL
9.8 8 reviews
Siesta Key, FL
09/07 – 11/07
£1319/nighttotal: £2638 (2 )

Bayside Escape | Water Views, Walk To Siesta Key Beach, Balcony & Community Pool

3 4
apartment , Siesta Key
This Siesta Key apartment, a 170 square metre (1830 square foot) self-catering property, is centrally located, within a 2.4 km radius of St Boniface Episcopal Church Labyrinth and Siesta Key Beach, and within 3.2 km of Siesta Key Beach Playground and Crescent Beach.
The three-bedroom, two-bathroom condo sleeps six guests and boasts a private balcony, swimming pool, tennis court, free Wi-Fi, and parking, alongside on-site barbecue grills and a water park.
New Listing! The Village Breeze 6br With Heated Pool, Near Beach, 250ft To Siesta Key Village! - Siesta Key, FL
10 2 reviews
Siesta Key, FL
05/07 – 11/07
£1358/nighttotal: £8148 (6 )

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

6 12
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.
Beautiful Large Home Bike To Siesta Key, Quiet Neighborhood With Local Owners! - Siesta Key, FL
9.8 60 reviews
Siesta Key, FL
14/07 – 11/08
£207/nighttotal: £5796 (28 )

Beautiful Large Home Bike To Siesta Key, Quiet Neighborhood With Local Owners!

3 3
apartment , Siesta Key
This spacious house is located just 2 kilometres from Siesta Key Beach in Sarasota, offering easy access to both the beach and local attractions. It has received excellent user ratings, making it a popular choice for travellers.
This three-bedroom, three-bathroom property spans 279 square metres and can comfortably accommodate up to eight guests. It boasts a range of amenities, including a spa, a garden, and a terrace, as well as a fully equipped kitchen and air conditioning.

Frequently asked questions about short term rentals in Siesta Key, FL

  • Which top landmarks shouldn't you miss in and around Siesta Key, FL?

    Well, you definitely want to check out Siesta Key Beach, it's famous for its soft, white sand. The Siesta Key Drum Circle is a must-see, especially on Sunday evenings. And if you're looking for something a little more historical, the Point of Rocks is a great spot to learn about the area's past.
  • What are the best short term rentals in Siesta Key, FL?

  • What types of short-term rentals are available in Siesta Key?

    When you are thinking of holidays in Siesta Key you would want to look for the best short-term rentals which would make things easier for you. This is important because you want to stay with your family and pet in a private space. Short-term rentals like condos, apartments and lofts and even townhouses provide you with the best private space you need when you are visiting Siesta Key. Choosing short-term rentals would also allow you to live in different neighbourhoods to make your stay convenient. If you are travelling with a pet you can make use of these rental properties which are pet-friendly and come with additional kitchen and bathroom facilities and amenities.
  • What notable natural landmarks are near Siesta Key, FL?

    You're in luck! Siesta Key is surrounded by beautiful natural landmarks. There's the Myakka River State Park, a great place for kayaking and hiking. And for a little more beach time, you can visit Turtle Beach, just a short drive away.
  • What are the best short term rentals with a pool in Siesta Key, FL?

  • What are the best kid-friendly attractions in Siesta Key?

    1. Siesta Key Beach - When you are in Siesta Key you would want to visit Siesta Key Beach with your kids where they can have a fun day playing in the sand and enjoying the sea.
    2. Mote Marine Laboratory and Aquarium - Taking your kids to an aquarium is a great way to spend a holiday. While this is a non-profit laboratory you can also find an aquarium featuring many marine animals and plant life.
    3. Siesta Key Village - When you have kids you can head to Siesta Key Village where you can shop and dine with the kids and take them to one of the many ice cream shops in the village.
  • What family-friendly activities are available near Siesta Key, FL?

    Siesta Key is a great place for families. There's the Siesta Key Beach, perfect for building sandcastles and splashing in the waves. For a fun day out, visit the Mote Marine Laboratory & Aquarium, where you can learn about marine life and see sharks, sea turtles, and more.
  • What are the best short term rentals with a jacuzzi in Siesta Key, FL?

  • What is the best neighbourhood to stay close to the city centre?

    If you prefer to stay close to the city centre you would want to look for accommodations in Reigels Landing which allows you to be just minutes away from the popular Siesta Key Beach. This means you can access the beach facilities and spend a day without having to commute much. Also, being here allows you to move around the island quickly and also access Stickney Point Road and explore Sarasota. Staying in Riegels Landing also allows you to enjoy the best local restaurants, bars and clubs close to the beach.
  • What kind of weather can travelers expect in Siesta Key, FL?

    Siesta Key has a subtropical climate, so expect warm temperatures year-round. Summers are hot and humid, with average temperatures around 30°C. Winters are mild, with average temperatures around 20°C. The best time to visit is during the spring or fall, when the weather is pleasant and the crowds are smaller.
  • What are the best short term rentals for families and kids in Siesta Key, FL?

  • What are the best shopping malls in Siesta Key?

    1. Southbridge Mall - If you are somewhere around Turtle Beach you can shop at the Southbridge Mall which has a good selection of shopping stores in Siesta Key.
    2. Sarasota Pavilion - When you are in Siesta Key you can also shop at the Sarasota Pavilion which is in Sarasota but close to Siesta Key. If you are looking for discount shopping and groceries this is where you can find the right options.
    3. Southbridge Plaza - When you intend to shop in Siesta Key you can head to Southbridge Plaza where you can find plenty of stores to shop on discounts.
  • What major cities can be found near Siesta Key, FL?

    Siesta Key is located near Sarasota, which is about a 15-minute drive. You can also easily reach Bradenton, which is about a 30-minute drive. Both cities offer a variety of attractions, restaurants, and shopping.
  • What is the best place to book a short-term rental for the Siesta Key Crystal Classic International Sand Sculpting Festival in Siesta Key?

    If you are planning to stay in Siesta Key for Siesta Key Crystal Classic International Sand Sculpting Festival you should look for short-term rentals in and around Riegels Landing. This would allow you to make the most of your accommodation. With plenty of short-term rentals in this area, you can choose from multiple condos, apartments and townhouses. Also, staying in the Riegels Landing neighbourhood would allow you to access Siesta Key Beach and various restaurants, cafes, bars and clubs around the beach. If you are looking for nightlife activities you can find plenty of venues here. With the best rental properties, you can stay privately and comfortably in Siesta Key and visit the event.

Destinations nearby

Discover Short-Term Rentals by the Sea in Siesta Key, FL

Base your upcoming coastal holiday at comfortable shoreside short-term rentals in Siesta Key, FL near the water.

111 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
10 11 reviews
Siesta Key, FL
23/06 – 30/06
£149/nighttotal: £1043 (7 )

111 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

2 2
apartment , Siesta Key
This apartment is located on Siesta Key's bay side, south of Sarasota, offering private access to Siesta Key Beach and a 5-10 minute walk to Siesta Village's shops and restaurants.
This 111 square meter condominium sleeps four guests in two bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, fitness centre, and a terrace, with beach chairs and toys provided for your use.

Best Siesta Key, FL short term rentals with a kitchen

Luxury Waterfront Views - Heated Pool - 1400sf Duplex - Minutes To The Beach - Siesta Key, FL
9.3 84 reviews
Siesta Key, FL
01/08 – 06/08
£253/nighttotal: £1265 (5 )

Luxury Waterfront Views - Heated Pool - 1400sf Duplex - Minutes To The Beach

2 5
apartment , Siesta Key
This Siesta Key duplex, a four-minute walk from Crescent Beach and 1.9 kilometres from Siesta Key Beach, offers easy access to Sarasota attractions such as the John and Mable Ringling Museum of Art (17.7 kilometres away) and the Sarasota Opera (12.4 kilometres away).
The 130 square metre property boasts a spacious two-bedroom, three-bathroom layout, a private heated pool, free parking, and on-site tennis facilities, perfect for a relaxing Siesta Key getaway.
Siesta Key Condo: Beach, Pool & Village Fun! - Siesta Key, FL
9.2 15 reviews
Siesta Key, FL
02/07 – 04/07
£375/nighttotal: £750 (2 )

Siesta Key Condo: Beach, Pool & Village Fun!

2 3
apartment , Siesta Key
This Siesta Key Village apartment is conveniently located a short 1.6km walk from Siesta Key Beach and the Farmers Market, with Irma Beach also within 3.2km.
The 71 square metre self-catering property features two bedrooms, one bathroom, sleeps four guests, and includes a private balcony, swimming pool, in-unit laundry, and free parking.
Walk To Beach/ Heated Pool/ New Listing Discount - Siesta Key, FL
9.2 10 reviews
Siesta Key, FL
27/06 – 11/07
£157/nighttotal: £2198 (14 )

Walk To Beach/ Heated Pool/ New Listing Discount

2 5
apartment , Siesta Key
This Siesta Key condo is located a short walk from Siesta Key Beach and steps from a community swimming pool, with Siesta Village's restaurants and shops also nearby.
The two-bedroom, two-bathroom apartment sleeps six guests and includes two bicycles, beach chairs, a wagon, umbrella, and toys, plus covered parking; a minimum one-week stay applies.
Casa Coquina | Luxury Home Steps To Crescent Beach - Siesta Key, FL
9.6 19 reviews
Siesta Key, FL
05/07 – 11/07
£632/nighttotal: £3792 (6 )

Casa Coquina | Luxury Home Steps To Crescent Beach

4 12
apartment , Siesta Key
Casa Coquina, a Siesta Key duplex, is situated less than 1.6km from Crescent Village, a three-minute walk from Crescent Beach and Point of Rocks, and a short drive from Siesta Key Village and Siesta Key Beach.
This four-bedroom, three-bathroom property sleeps up to 14 guests and boasts a private heated pool (heated Nov 15th-Apr 15th), a cabana, ping pong table, outdoor dining areas, beach gear, and free Wi-Fi; one well-behaved dog under 25lbs is welcome (fee applies).

Best Siesta Key, FL short term rentals with laundry available

Pink Mango Cottage Steps From The Beach - Siesta Key, FL
10 15 reviews
Siesta Key, FL
16/07 – 19/07
£292/nighttotal: £876 (3 )

Pink Mango Cottage Steps From The Beach

2 2
apartment , Siesta Key
Private Suite + Workspace Near Siesta Beach - Siesta Key, FL
9.5 111 reviews
Siesta Key, FL
10/07 – 12/07
£115/nighttotal: £230 (2 )

Private Suite + Workspace Near Siesta Beach

1 2
apartment , Siesta Key
Siesta Key Beach - 2 Bedroom - 3 Beds - 3 Bathroom Duplex With Heated Swimming Pool - Siesta Key, FL
9.2 148 reviews
Siesta Key, FL
25/12 – 02/01
£327/nighttotal: £2616 (8 )

Siesta Key Beach - 2 Bedroom - 3 Beds - 3 Bathroom Duplex With Heated Swimming Pool

2 5
apartment , Siesta Key
Coastal Condo, Water Views, Fishing Dock & 0.6 Miles To Siesta Beach - Siesta Key, FL
10 5 reviews
Siesta Key, FL
23/06 – 30/06
£165/nighttotal: £1155 (7 )

Coastal Condo, Water Views, Fishing Dock & 0.6 Miles To Siesta Beach

2 2
apartment , Siesta Key

Handpicked Short-Term Rentals with Parking in Siesta Key, FL

Driving to Siesta Key, FL? Each short-term let here includes parking, making reaching the coast simple from the moment you arrive.

Bay View Condo, Minutes To Top Beach In The Us - Siesta Key, FL
9.2 49 reviews
Siesta Key, FL
06/07 – 13/07
£123/nighttotal: £861 (7 )

Bay View Condo, Minutes To Top Beach In The Us

2 2
apartment , Siesta Key
Newly Renovated Condo Steps From Sk Private Beach - Siesta Key, FL
9.7 113 reviews
Siesta Key, FL
08/07 – 10/07
£469/nighttotal: £938 (2 )

Newly Renovated Condo Steps From Sk Private Beach

1 4
apartment , Siesta Key
Ground-level Condo | Beach Access, Pool & Canal Views | Walk To Everything - Siesta Key, FL
9.2 27 reviews
Siesta Key, FL
06/07 – 13/07
£241/nighttotal: £1687 (7 )

Ground-level Condo | Beach Access, Pool & Canal Views | Walk To Everything

2 3
apartment , Siesta Key
Walk To The Beach And Village - Hibiscus Villa - Siesta Key, FL
9.0 6 reviews
Siesta Key, FL
13/07 – 17/07
£206/nighttotal: £824 (4 )

Walk To The Beach And Village - Hibiscus Villa

1 2
apartment , Siesta Key

Explore Short-Term Rentals with a Hot Tub in Siesta Key, FL

These short-term lets near the water in Siesta Key, FL come with a hot tub or jacuzzi, ideal for a private hot tub soak after a.

Luxury 4br Home With Private Pool Siesta Key - Siesta Key, FL
Siesta Key, FL
14/08 – 21/08
£598/nighttotal: £4186 (7 )

Luxury 4br Home With Private Pool Siesta Key

4 8
apartment , Siesta Key
Siesta Key Escape Ground Floor Steps To Heated Pool And Free Trolley - Siesta Key, FL
8.8 82 reviews
Siesta Key, FL
07/09 – 14/09
£200/nighttotal: £1400 (7 )

Siesta Key Escape Ground Floor Steps To Heated Pool And Free Trolley

2 5
apartment , Siesta Key
Lj's Cottages 1 - Pool Beach Sunset - Siesta Key, FL
9.8 7 reviews
Siesta Key, FL
04/09 – 08/09
£370/nighttotal: £1480 (4 )

Lj's Cottages 1 - Pool Beach Sunset

2 8
apartment , Siesta Key
Gertrude's Siesta | Pool, Jacuzzi! 1-minute To Beach! 4-min Dining & Music! - Siesta Key, FL
10 12 reviews
Siesta Key, FL
04/07 – 08/07
£573/nighttotal: £2292 (4 )

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

2 4
apartment , Siesta Key
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