Siesta Key, FL Short term rentals

4040 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Siesta Key, FL short term rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Siesta Key, FL

Best Siesta Key, FL short term rentals with a balcony

Condo# 219 Siesta Key Paradise Unit 219 - Siesta Key, FL
9.2 16 reviews
Siesta Key, FL
30/07 – 09/08
£209/nighttotal: £2090 (10 )

Condo# 219 Siesta Key Paradise Unit 219

2 5
apartment , Siesta Key
This Siesta Key apartment, less than 2km from Siesta Key Beach, Siesta Key Farmers Market, and St. Boniface Episcopal Church Labyrinth, offers convenient access to local attractions.
This 81-square-metre, two-bedroom, one-bathroom condo sleeps six and boasts a private pool, fitness centre, tennis court, and on-site amenities including a barbecue area and games room.
Beachside Villa In Siesta Key | Canal Front | Pool - Siesta Key, FL
9.8 19 reviews
Siesta Key, FL
12/07 – 18/07
£217/nighttotal: £1302 (6 )

Beachside Villa In Siesta Key | Canal Front | Pool

1 2
apartment , Siesta Key
This Siesta Key Village holiday home is less than 1.6km from Siesta Key Beach and within 3.2km of the Siesta Key Farmers Market.
The two-bedroom, one-bathroom property sleeps four, boasting a fully equipped kitchen with fridge and microwave, a washing machine, balcony, and amenities including a TV and coffee maker.
Great Siesta Key Location With Deeded Beach Access At The Anchorage 308 - Siesta Key, FL
9.0 21 reviews
Siesta Key, FL
15/08 – 22/08
£173/nighttotal: £1211 (7 )

Great Siesta Key Location With Deeded Beach Access At The Anchorage 308

2 6
apartment , Siesta Key
This Siesta Key condo, located in The Anchorage, boasts deeded beach access to Crescent Beach and is within walking distance of Siesta Key's shops and restaurants.
The 120-square-metre (1292 sq ft) apartment features a spacious three-bedroom, two-bathroom layout sleeping six, with a private balcony overlooking a waterway, a well-equipped kitchen, and access to resort amenities including a heated pool, tennis courts, and a sauna.
Gertrude Siesta | Private Patios, Beach & Village, 100 Steps To Best Views On Siesta Key - Siesta Key, FL
9.7 168 reviews
Siesta Key, FL
14/08 – 21/08
£390/nighttotal: £2730 (7 )

Gertrude Siesta | Private Patios, Beach & Village, 100 Steps To Best Views On Siesta Key

3 8
apartment , Siesta Key
This family-friendly holiday home is located in Siesta Key, just a mile from Irma Beach and Siesta Key Beach, and within a three-mile radius of Shell Beach and St. Boniface Episcopal Church Labyrinth. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The accommodation has three bedrooms and three bathrooms, comfortably accommodating up to ten guests. The house offers a range of amenities including a fully equipped kitchen, a swimming pool, a garden, a tennis court, and a water park, providing ample opportunities for relaxation and entertainment.

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.

112 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
10 1 review
Siesta Key, FL
06/07 – 13/07
£193/nighttotal: £1351 (7 )

112 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

2 3
apartment , Siesta Key
This two-bedroom flat in the Gulf & Bay Club Bayside community offers direct intercoastal waterway frontage, providing views of marine life and is a short 500-meter walk from Siesta Key Village and the beach.
This 111-square-meter apartment accommodates up to four guests and features resort-style amenities including two heated swimming pools, tennis and pickleball courts, a fitness centre, and secure garage parking.
Perfect Location Sk Village Condo 2 Br Short Walk To Beach, Pool Arcade Pets Ok - Siesta Key, FL
9.4 14 reviews
Siesta Key, FL
01/08 – 08/08
£243/nighttotal: £1701 (7 )

Perfect Location Sk Village Condo 2 Br Short Walk To Beach, Pool Arcade Pets Ok

2 5
apartment , Siesta Key
This Siesta Key apartment, a short 1.6km stroll from Siesta Key Beach and the Siesta Key Farmers' Market, offers easy access to Irma and Shell Beaches within a 3.2km radius.
The 71 square metre self-catering property sleeps four guests in two bedrooms and one bathroom, boasting a private patio, swimming pool, and in-unit laundry facilities.
400 Yards To Siesta Key Village, 800 Yard To The Public Beach Access 2 And 7. - Siesta Key, FL
9.8 53 reviews
Siesta Key, FL
22/06 – 29/06
£486/nighttotal: £3402 (7 )

400 Yards To Siesta Key Village, 800 Yard To The Public Beach Access 2 And 7.

3 6
apartment , Siesta Key
This Siesta Key holiday home is located just 3 kilometres from Siesta Key Beach, Irma Beach, and St. Boniface Episcopal Church Labyrinth, offering a convenient base for exploring the area. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This 3-bedroom property comfortably accommodates up to 8 guests, making it ideal for families or groups of friends. The house boasts a range of amenities, including a fitness centre, spa tub, and a fenced private yard, ensuring a relaxing and enjoyable stay.
Gertrude's Siesta | 1 Min Walk To Beach Path | Free Bikes, Boards & Trolley! - Siesta Key, FL
9.6 86 reviews
Siesta Key, FL
01/08 – 09/08
£239/nighttotal: £1912 (8 )

Gertrude's Siesta | 1 Min Walk To Beach Path | Free Bikes, Boards & Trolley!

1 2
apartment , Siesta Key
This family-friendly apartment is located on Siesta Key, just 1.6 kilometres from Siesta Key Beach and St. Boniface Episcopal Church Labyrinth. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The apartment has one bedroom and one bathroom, accommodating up to four guests. It features a fully equipped kitchen, a washing machine, a terrace, and a garden, making it a comfortable and convenient choice for families and groups.

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.

Siesta Beach 3 Min | Walk To Village + Patio! - Siesta Key, FL
10 1 review
Siesta Key, FL
04/07 – 08/07
£238/nighttotal: £952 (4 )

Siesta Beach 3 Min | Walk To Village + Patio!

1 4
apartment , Siesta Key
This Siesta Key flat is perfectly situated a mere 270 metres from the award-winning Siesta Key beaches and an 8-minute stroll to the Village's diverse dining and entertainment establishments.
This family-friendly apartment accommodates up to four guests and boasts on-site amenities including a heated swimming pool, a games room with ping-pong and billiards, and complimentary beach gear.

Best Siesta Key, FL short term rentals with a kitchen

Condo# 204 2 Bedroom 1 Bath Condo Is Steps To The White Powdered  Sand Of Siesta Key - Siesta Key, FL
9.3 30 reviews
Siesta Key, FL
05/07 – 12/07
£243/nighttotal: £1701 (7 )

Condo# 204 2 Bedroom 1 Bath Condo Is Steps To The White Powdered Sand Of Siesta Key

2 5
apartment , Siesta Key
This two-bedroom apartment is located in La Siesta Condominiums, just a short walk from the famous Siesta Key Beach and a few minutes from the lively Siesta Village. It has received excellent user and location ratings and a very good cleanliness rating.
The 81 square metre apartment can accommodate up to six guests and features a fully equipped kitchen, a private balcony with beach views, and a screened lanai. Amenities include air conditioning, a swimming pool, a fitness centre, a tennis court, and parking.
Beechwood  Suites  C - Siesta Key, FL
10 5 reviews
Siesta Key, FL
15/08 – 19/08
£181/nighttotal: £724 (4 )

Beechwood Suites C

2 5
apartment , Siesta Key
This Siesta Key apartment is conveniently located near Siesta Key Marina and Crescent Beach, a 15-minute walk away, and within 4.8km of Siesta Key Beach and Turtle Beach.
This two-bedroom, two-bathroom dwelling sleeps six, offering in-unit laundry facilities, a swimming pool, and essential amenities; explore nearby Sarasota's attractions from this relaxing base.
Relaxing Siesta Key Condo - Siesta Key, FL
9.7 100 reviews
Siesta Key, FL
12/09 – 19/09
£149/nighttotal: £1043 (7 )

Relaxing Siesta Key Condo

2 3
apartment , Siesta Key
This apartment is located on Siesta Key, just across the street from Crescent Beach and a short walk from the Siesta Key Village, offering easy access to the island's best attractions. The accommodation has excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment is a two-bedroom property, spanning 80 square meters and comfortably accommodating up to four guests. It features a fully equipped kitchen, a private balcony with breathtaking waterfront views, and access to a range of on-site amenities including a swimming pool, fitness centre, and tennis courts.
Luxury Condo With Heated Pools, Amazing Beach View - Siesta Key, FL
9.0 4 reviews
Siesta Key, FL
14/07 – 11/08
£110/nighttotal: £3080 (28 )

Luxury Condo With Heated Pools, Amazing Beach View

2 3
apartment , Siesta Key
This two-bedroom, two-bathroom condominium offers direct Intracoastal Waterway access in Siesta Key, just 100 metres from the renowned powdery sands of Siesta Key Beach and a short trolley ride to Siesta Key Village's dining and shopping.
Guests can enjoy resort-style amenities including two heated swimming pools and a fitness room, with the option to register for on-site boat docking, accommodating up to six people with a private balcony providing coastal views.

Best Siesta Key, FL short term rentals with laundry available

Chic Peaceful 3bd Cottage - Walk To Siesta! - Siesta Key, FL
9.2 13 reviews
Siesta Key, FL
14/07 – 11/08
£66/nighttotal: £1848 (28 )

Chic Peaceful 3bd Cottage - Walk To Siesta!

2 3
apartment , Siesta Key
2br Siesta Key Condo - Beach Access - Gbb 1340 - Siesta Key, FL
9.4 7 reviews
Siesta Key, FL
25/07 – 30/07
£269/nighttotal: £1345 (5 )

2br Siesta Key Condo - Beach Access - Gbb 1340

2 5
apartment , Siesta Key
Our House At The Beach By Tropical Sands - Siesta Key, FL
10 1 review
Siesta Key, FL
25/07 – 30/07
£255/nighttotal: £1275 (5 )

Our House At The Beach By Tropical Sands

2 5
apartment , Siesta Key
Across From Beach, Stunning Canal Views, Age 55 Up - Siesta Key, FL
10 3 reviews
Siesta Key, FL
14/07 – 11/08
£98/nighttotal: £2744 (28 )

Across From Beach, Stunning Canal Views, Age 55 Up

2 3
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.

Vacation Home Away From Home At Bay Oaks D41 - Siesta Key, FL
9.6 10 reviews
Siesta Key, FL
14/07 – 11/08
£152/nighttotal: £4256 (28 )

Vacation Home Away From Home At Bay Oaks D41

2 3
apartment , Siesta Key
Relaxing 2br Siesta Key Condo With Beach Access - Gbb 1365 - Siesta Key, FL
10 4 reviews
Siesta Key, FL
06/07 – 13/07
£201/nighttotal: £1407 (7 )

Relaxing 2br Siesta Key Condo With Beach Access - Gbb 1365

2 3
apartment , Siesta Key
Gertrude Siesta | 8-steps Beach Path, 4-min Dining - Siesta Key, FL
8.7 3 reviews
Siesta Key, FL
04/07 – 11/07
£549/nighttotal: £3843 (7 )

Gertrude Siesta | 8-steps Beach Path, 4-min Dining

3 12
apartment , Siesta Key
Gulf Holiday Unit 8 - Siesta Key, FL
Siesta Key, FL
16/07 – 19/07
£294/nighttotal: £882 (3 )

Gulf Holiday Unit 8

1 2
house , 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.

Caribbean Dream | Luxury Condo On Sk W Heated Pool - Siesta Key, FL
10 12 reviews
Siesta Key, FL
03/09 – 11/09
£263/nighttotal: £2104 (8 )

Caribbean Dream | Luxury Condo On Sk W Heated Pool

2 3
apartment , Siesta Key
Siesta Key Beach Resort And Suites - Siesta Key, FL
8.8 2540 reviews
Siesta Key, FL
06/07 – 13/07
£292/nighttotal: £2044 (7 )

Siesta Key Beach Resort And Suites

1 2
house , Siesta Key
Siesta Bliss ~ Luxury Waterfront Retreat - Siesta Key, FL
10 11 reviews
Siesta Key, FL
14/08 – 21/08
£622/nighttotal: £4354 (7 )

Siesta Bliss ~ Luxury Waterfront Retreat

1 8
apartment , Siesta Key
Siesta Dunes 7-102 By Siesta Dunes - Siesta Key, FL
Siesta Key, FL
12/07 – 19/07
£428/nighttotal: £2996 (7 )

Siesta Dunes 7-102 By Siesta Dunes

2 5
apartment , Siesta Key
©2026 cozycozy.com