Holiday Rentals in Siesta Key, FL

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Siesta Key, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Siesta Key, FL

Best family friendly Siesta Key, FL holiday rentals

Among the 5754 accommodations in Siesta Key, FL, here are the 4 best family friendly rentals

Welcome To Siesta Dreams At Casa Mar!! - Siesta Key, FL
9.6 68 reviews
Siesta Key, FL
31/10 – 07/11
£173/nighttotal: £1211 (7 )

Welcome To Siesta Dreams At Casa Mar!!

1 4
apartment , Siesta Key
This Siesta Key beachfront apartment, situated less than 1.6km from Siesta Key Beach and Crescent Beach, also offers easy access to St. Boniface Episcopal Church Labyrinth and Siesta Key Marina.
The 56 square metre property comprises two bedrooms, one bathroom, sleeps four guests, and features a fully equipped kitchen, private patio, swimming pool access, and free Wi-Fi.
Heated Pool-short Walk To Beach, Free Trolley Around Siesta Key! - Siesta Key, FL
9.3 27 reviews
Siesta Key, FL
03/09 – 11/09
£163/nighttotal: £1304 (8 )

Heated Pool-short Walk To Beach, Free Trolley Around Siesta Key!

2 3
apartment , Siesta Key
This apartment is situated in Siesta Key, just a short walk from Crescent Beach and a little over 1.6 kilometres from Siesta Key Beach. The apartment has received very good user ratings, with excellent reviews for its location and cleanliness.
The apartment is a two-bedroom property, covering 102 square metres and accommodating up to four guests. Guests can enjoy a range of amenities, including a swimming pool, tennis court, sauna, and a garden, as well as a balcony with pool views.
Bayside Escape | Water Views, Walk To Siesta Key Beach, Balcony & Community Pool - Siesta Key, FL
9.8 8 reviews
Siesta Key, FL
19/06 – 21/06
£1148/nighttotal: £2296 (2 )

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

3 6
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.
Oceanview 100 Percent Private, Tiki, 100ft To Beach Path! - Siesta Key, FL
Siesta Key, FL
01/07 – 04/07
£3322/nighttotal: £9966 (3 )

Oceanview 100 Percent Private, Tiki, 100ft To Beach Path!

7 2
house , Siesta Key
This seven-bedroom Siesta Key holiday home is situated a short walk from Siesta Key Beach and a 2.25 km stroll from Crescent Beach, offering easy access to Sarasota's attractions, including the Ringling Museum (16 km) and Sarasota Opera House (10.8 km).
The 251-square-metre property boasts a spacious layout with three living rooms, five bathrooms, a fully equipped kitchen, private parking, free Wi-Fi, and accommodates up to 47 guests.

Find the Best Holiday Rentals with a Pool in Siesta Key, FL

Pool access at your holiday rental in Siesta Key, FL provides the perfect complement to a day by the water. Find your ideal stay here.

Cozy Gem On Siesta Key – Nice Walk To Beach & Bay! - Siesta Key, FL
9.5 103 reviews
Siesta Key, FL
06/07 – 13/07
£168/nighttotal: £1176 (7 )

Cozy Gem On Siesta Key – Nice Walk To Beach & Bay!

1 2
apartment , Siesta Key
This Siesta Key condo is located on the east side of Midnight Pass Road, approximately 1 kilometre from Siesta Key Beach's access point #12.
The one-bedroom apartment, sleeping up to four guests, boasts a private lanai, in-unit laundry, reserved parking, and access to a community pool, tennis courts, and BBQ area; beach equipment is also provided.
Ground-level Condo | Beach Access, Pool & Canal Views | Walk To Everything - Siesta Key, FL
9.2 27 reviews
Siesta Key, FL
01/08 – 08/08
£232/nighttotal: £1624 (7 )

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

2 2
apartment , Siesta Key
This Siesta Key beachfront apartment offers stunning ocean views and is less than 1.6km from Siesta Key Beach and Crescent Beach, and within 1.6km of Siesta Key Marina and Point of Rocks.
The 80 square metre property boasts two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, swimming pool, fitness centre, tennis court, and parking.
6415 Midnight Pass #606 - Siesta Key, FL
8.3 3 reviews
Siesta Key, FL
25/07 – 30/07
£265/nighttotal: £1325 (5 )

6415 Midnight Pass #606

2 5
house , Siesta Key
6415 Midnight Pass #606, a Siesta Key holiday home, is conveniently located a short walk from Crescent Beach and within 2.6 km of Turtle Beach and Siesta Key Beach.
This 116 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, jacuzzi, sauna, fitness centre, and tennis court, alongside a fully equipped kitchen and free Wi-Fi.
Siesta Key Village, Pool, Beach Access 4-min Walk - Siesta Key, FL
9.9 53 reviews
Siesta Key, FL
01/07 – 04/07
£279/nighttotal: £837 (3 )

Siesta Key Village, Pool, Beach Access 4-min Walk

1 2
apartment , Siesta Key
This one-bedroom Siesta Key Village townhouse is a ten-step walk from shops and restaurants, and a five-minute walk (approximately 0.4 km) from Siesta Key Beach.
The self-catering apartment sleeps four, boasts a fully equipped kitchen including a Keurig coffee machine, a shared heated pool, and complimentary beach essentials (towels, chairs, umbrella, and cart), plus on-site guest services.

Frequently asked questions about holiday rentals in Siesta Key, FL

  • What are some interesting places to visit in or near Siesta Key, FL?

    Siesta Key is known for its beautiful beaches, but there are also plenty of other interesting places to visit. The Siesta Key Drum Circle is a popular spot for live music and entertainment, and you can also visit the Siesta Key Village for shopping and dining. If you're looking for something a bit further afield, you can take a trip to the nearby city of Sarasota, which has a number of museums and art galleries.
  • What are the best Airbnb and holiday rentals in Siesta Key, FL?

  • Which walking or cycling routes are the best in Siesta Key, FL?

    For walking and cycling, the Siesta Key Beach is a great choice. The paved path stretches for 3.5km along the beach, offering stunning views of the Gulf of Mexico. You can also explore the residential areas of Siesta Key, which are full of charming shops and restaurants. For a more challenging ride, consider the Legacy Trail, which runs for 12.5km from Sarasota to Venice.
  • What are the most popular Airbnbs in Siesta Key, FL?

  • What sports or outdoor activites can visitors enjoy in and around Siesta Key, FL?

    Siesta Key is a paradise for outdoor enthusiasts. You can swim, sunbathe, and surf on the beautiful beaches, or try your hand at kayaking or paddleboarding in the calm waters of the Gulf of Mexico. There are also plenty of opportunities for fishing, both from the shore and from a boat. If you're looking for something a bit more adventurous, you can go parasailing or jet skiing.
  • What are the best holiday rentals with a pool in Siesta Key, FL?

  • What other towns or cities can be easily accessed from Siesta Key, FL?

    Siesta Key is conveniently located near several other towns and cities. Sarasota, a vibrant city with a thriving arts scene, is just a short drive away. You can also easily reach Venice, known for its beautiful beaches and historic downtown, and Bradenton, home to the famous Robinson Preserve.
  • What are the best rentals for families and kids in Siesta Key, FL?

  • What amenities are commonly available in vacation rentals in Siesta Key, FL?

    Vacation rentals in Siesta Key typically offer a range of amenities, including private pools, hot tubs, and outdoor grills. Many also have fully equipped kitchens, laundry facilities, and high-speed internet access. Some rentals even offer beach access, making it easy to enjoy the beautiful beaches of Siesta Key.
  • What are the best rentals or Airbnbs with a jacuzzi in Siesta Key, FL?

  • What time of year is best to rent a vacation rental Siesta Key, FL?

    The best time to visit Siesta Key is during the spring or autumn months, when the weather is pleasant and the crowds are smaller. However, if you're looking for a beach vacation, you can enjoy Siesta Key year-round. Just be aware that the summer months can be very hot and humid, and the winter months can be cool and rainy.
  • What are the local dishes in Siesta Key, FL region?

    Siesta Key is known for its fresh seafood, and you'll find plenty of restaurants serving up delicious dishes like grouper sandwiches, shrimp scampi, and stone crabs. You can also enjoy classic American cuisine, such as burgers, fries, and pizza. For a taste of local flavour, try the Key lime pie, a refreshing dessert made with Key lime juice.

Destinations nearby

Best Siesta Key, FL holiday rentals with a balcony

Charming 2br Condo Pool View ~ Siesta Key Bay Oaks - Siesta Key, FL
9.2 32 reviews
Siesta Key, FL
31/10 – 07/11
£184/nighttotal: £1288 (7 )

Charming 2br Condo Pool View ~ Siesta Key Bay Oaks

2 4
apartment , Siesta Key
This Siesta Key condo, a 102-square-metre (1100 sq ft) apartment, is situated less than 1.6km from Siesta Key Beach and Crescent Beach, and under 1.6km from Siesta Key Marina.
The two-bedroom, two-bathroom property sleeps eight, boasting a fully equipped kitchen, private terrace, swimming pool, parking, and internet access; nearby attractions include the St. Boniface Episcopal Church Labyrinth.
Rent This Luxury 5 Star Apartment On The Anchorage, Siesta Key Apartment 1029 - Siesta Key, FL
9.4 12 reviews
Siesta Key, FL
15/08 – 22/08
£266/nighttotal: £1862 (7 )

Rent This Luxury 5 Star Apartment On The Anchorage, Siesta Key Apartment 1029

2 6
apartment , Siesta Key
This Siesta Key apartment is located just a short walk from the marina and Crescent Beach, and less than 1.6km from the famous Siesta Key Beach, offering easy access to the island's top attractions. It has received excellent user and location ratings, as well as a very good cleanliness rating.
The apartment has two bedrooms and two bathrooms, spanning 116 square meters, and comes equipped with a modern kitchen, a terrace, a swimming pool, a sauna, a spa, a fitness centre, and parking. Guests can enjoy the convenience of in-room amenities like a TV and a dryer, as well as the option of housekeeping on request.
Newly Remodeled 3bd/3bh | 10 Mins To The Beach - Siesta Key, FL
9.4 35 reviews
Siesta Key, FL
01/07 – 04/07
£311/nighttotal: £933 (3 )

Newly Remodeled 3bd/3bh | 10 Mins To The Beach

3 9
apartment , South Sarasota
This modern, newly renovated three-bedroom apartment is located in central Sarasota, just 4.8 kilometres from Siesta Key and 6.4 kilometres from downtown Sarasota. The apartment has received excellent reviews from previous guests.
The apartment spans 186 square metres and comfortably accommodates up to 10 guests. It boasts a range of amenities, including a fully equipped kitchen, a private garden, a terrace, and parking for trailers, boats, or RVs.
Siesta Key Beach Condo #1 Beach - Siesta Key, FL
8.2 39 reviews
Siesta Key, FL
21/06 – 28/06
£160/nighttotal: £1120 (7 )

Siesta Key Beach Condo #1 Beach

1 3
apartment , Siesta Key
This one-bedroom apartment is situated on Siesta Key, just 1.6 kilometres from Siesta Key Beach and 3.2 kilometres from Crescent Beach. The location is peaceful and offers easy access to the island's most popular destinations. The apartment has received very good user ratings.
The apartment has a comfortable living space with a sofa bed, perfect for a family of three. Guests can enjoy a private pool, a shared outdoor pool, a garden, a balcony, free Wi-Fi, and a kitchen with a fridge and microwave.

Our Favourite Holiday Rentals with Parking in Siesta Key, FL

A car park at your holiday rental in Siesta Key, FL makes reaching the coast and local beaches easy every day with no extra faff.

Walk To Siesta Village, Heated Saltwater Pool - Siesta Key, FL
10 65 reviews
Siesta Key, FL
27/07 – 29/07
£444/nighttotal: £888 (2 )

Walk To Siesta Village, Heated Saltwater Pool

1 4
apartment , Siesta Key
This Siesta Key holiday home, a short 0.8km stroll from Siesta Key Village, offers easy access to restaurants, nightlife, and shops.
The three-bedroom, two-bathroom property sleeps six, boasting a heated saltwater pool, fully fenced garden, Blackstone grill, and beach essentials including chairs, cooler, and bicycles; hurricane-resistant location.
Canal 315 - Right In Siesta Key Village! - Siesta Key, FL
9.0 176 reviews
Siesta Key, FL
01/08 – 09/08
£378/nighttotal: £3024 (8 )

Canal 315 - Right In Siesta Key Village!

2 2
house , Siesta Key
Canal 313, a renovated holiday home in Siesta Key Village, is situated a short distance from Siesta Key Beach and 2.1 kilometres from Crescent Beach, offering easy access to local amenities and the Ringling Museum of Art (within 16 kilometres).
This 93-square-metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, a private swimming pool, tennis court, free Wi-Fi, and parking; ideal for families or small groups seeking a relaxing Siesta Key getaway.
The Beach Club At Siesta #106d - Siesta Key, FL
10 1 review
Siesta Key, FL
25/07 – 30/07
£285/nighttotal: £1425 (5 )

The Beach Club At Siesta #106d

1 5
house , Siesta Key
This holiday cottage in Point O'Rocks, Siesta Key, offers direct access to Crescent Beach, situated 17.7 kilometres from the John and Mable Ringling Museum of Art and 19.3 kilometres from Sarasota International Convention Centre.
This 75 square metre villa accommodates up to 11 guests with 2 bathrooms, featuring a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, jacuzzi, garden, fitness centre, tennis court, and private parking, with cycling opportunities nearby.
Dream Sunsets & Coastal Blissbeach Club 108a / Rva - Siesta Key, FL
8.9 84 reviews
Siesta Key, FL
21/10 – 25/10
£262/nighttotal: £1048 (4 )

Dream Sunsets & Coastal Blissbeach Club 108a / Rva

2 3
apartment , Siesta Key
The Beach Club At Siesta Key #108a Resort By Rva is situated directly on Siesta Key, within a mile of both Crescent Beach and Siesta Key Beach. This property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom apartment can accommodate up to six guests, making it ideal for families or groups. The apartment is equipped with a range of amenities including a swimming pool, Jacuzzi, terrace, garden, tennis court, parking, and free WiFi, providing everything you need for a relaxing and enjoyable holiday.
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