Holiday Rentals in Siesta Key, FL

5754 available vacation rental offers

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

5754 Holiday rentals and Airbnb 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

Siesta Key Cottages Crescent 2a Beach/pool/hot Tub - Siesta Key, FL
9.7 393 reviews
Siesta Key, FL
08/07 – 10/07
352 €/nighttotal: 704 € (2 )

Siesta Key Cottages Crescent 2a Beach/pool/hot Tub

2 4
apartment , Siesta Key
This charming cottage is situated a mere 0.6km from the renowned Siesta Key Beach, known as Crescent Beach, offering a tranquil setting close to the most beautiful part of the island. With excellent user, location, and cleanliness ratings, this cottage promises a comfortable and enjoyable stay.
The cottage comfortably sleeps six, making it ideal for families or groups. Guests can enjoy a range of amenities, including two heated pools, two hot tubs, two outdoor gyms, free bikes, beach equipment, private porches, grills, fire pits, and outdoor showers.
139 M² House ∙ 3 Bedrooms ∙ 10 Guests - Siesta Key, FL
9.8 26 reviews
Siesta Key, FL
02/07 – 04/07
1609 €/nighttotal: 3218 € (2 )

139 M² House ∙ 3 Bedrooms ∙ 10 Guests

3 3
house , Siesta Key
Casita Sun Star, a three-bedroom duplex in South Siesta Key, is situated a 0.2-kilometre walk from Crescent Beach and Point of Rocks, with Siesta Key Village and Siesta Key Beach a short drive away.
This 139-square-metre property sleeps up to 10 guests, boasting a private heated pool (heated 15 November–15 April), three bathrooms, a fully equipped kitchen, free Wi-Fi, and four HDTVs; one well-behaved dog (up to 11 kg) is welcome for a fee.
Fiesta In Siesta Key! Fun & Sun - Siesta Key, FL
9.8 88 reviews
Siesta Key, FL
12/09 – 19/09
115 €/nighttotal: 805 € (7 )

Fiesta In Siesta Key! Fun & Sun

1 2
apartment , Siesta Key
This Siesta Key beachfront apartment is directly opposite Siesta Key Beach and within 800 metres of restaurants including Mango Cafe and Anna's Famous Deli.
The two-bedroom, two-bathroom property sleeps five, offering a fully equipped kitchen with a Keurig coffee maker, a living room with Smart TV, and beach amenities including chairs, towels, and umbrellas; on-site laundry and 5-star management are also available.
Beach Rd, 300ft To Beach Access & 500ft To Village - Siesta Key, FL
9.9 44 reviews
Siesta Key, FL
27/06 – 01/07
201 €/nighttotal: 804 € (4 )

Beach Rd, 300ft To Beach Access & 500ft To Village

1 2
apartment , Siesta Key
This Siesta Key studio apartment is situated a mere 0.06 km from Siesta Key Beach and a 0.4 km stroll from Siesta Village, offering easy access to restaurants, shops, and entertainment.
The self-catering unit features a queen-sized bed, a kitchen with fridge, freezer, and microwave, sleeps two guests, and includes free high-speed internet, beach equipment, and on-site parking.

Best Siesta Key, FL holiday rentals with a pool

Among the 5754 accommodations in Siesta Key, FL, here are the 4 best rentals with a pool

Cozy Cottage Near Siesta Key Village! - Siesta Key, FL
9.0 2 reviews
Siesta Key, FL
09/08 – 15/08
295 €/nighttotal: 1770 € (6 )

Cozy Cottage Near Siesta Key Village!

1 4
cottage , Siesta Key
This cottage in Siesta Key is located just 150 metres from Siesta Beach and a short walk from Siesta Key Village.
This 51 square metre holiday home sleeps four guests and features two bedrooms, one bathroom, a private kitchen and living room, with access to a shared swimming pool and hot tub, plus complimentary bicycle rentals and beach equipment.
Topsail Cottage | Luxury Home On Siesta Key W/ Heated Pool & Rooftop View Of Gulf, Walk To Beach! - Siesta Key, FL
9.8 42 reviews
Siesta Key, FL
24/06 – 28/06
876 €/nighttotal: 3504 € (4 )

Topsail Cottage | Luxury Home On Siesta Key W/ Heated Pool & Rooftop View Of Gulf, Walk To Beach!

4 2
apartment , Siesta Key
This Siesta Key beachfront property is located less than 1.6km from Siesta Key Beach and Point of Rocks, with Crescent Beach and Siesta Key Marina within a 15-minute drive.
This four-bedroom, four-bathroom holiday home boasts 311 square metres of living space, sleeps up to 12 guests, includes a private swimming pool, rooftop terrace with gas grills, and offers stunning ocean views.
2025 Completely Remodeled Private Villa, 7 Min Walk To Beach, Entertainment - Siesta Key, FL
9.9 38 reviews
Siesta Key, FL
24/06 – 01/07
261 €/nighttotal: 1827 € (7 )

2025 Completely Remodeled Private Villa, 7 Min Walk To Beach, Entertainment

2 6
house , Siesta Key
This Siesta Key single-family home enjoys a private yet convenient location, close to Siesta Key's attractions and amenities.
The 111 square metre, single-storey property sleeps seven comfortably, boasting two bedrooms, two bathrooms, a fully equipped kitchen, a private pool, and a Weber gas grill for al fresco dining; beach essentials are included.
Awesome 2bd Condo Near The Beach (An799) - Siesta Key, FL
9.3 46 reviews
Siesta Key, FL
09/08 – 15/08
249 €/nighttotal: 1494 € (6 )

Awesome 2bd Condo Near The Beach (An799)

2 4
apartment , Siesta Key
This apartment is located just a short walk from Crescent Beach and less than 1.6km from Siesta Key Beach, offering easy access to the area's beautiful beaches and vibrant atmosphere. The property has received excellent ratings for location, cleanliness and overall user experience.
The two-bedroom apartment comfortably accommodates six guests and features a balcony, two bathrooms, and a fully equipped kitchen. Guests can enjoy amenities such as a swimming pool, tennis court, fitness centre, sauna and spa, as well as free parking and internet access.

Frequently asked questions about holiday rentals in Siesta Key, FL

Destinations nearby

Best Siesta Key, FL holiday rentals with a balcony

6415 Midnight Pass #210 - Siesta Key, FL
Siesta Key, FL
04/07 – 09/07
357 €/nighttotal: 1785 € (5 )

6415 Midnight Pass #210

2 3
house , Siesta Key
This Siesta Key holiday home, 6415 Midnight Pass #210, is a 7-minute walk from Crescent Beach, 2.6 km from Turtle Beach, and 2.9 km from Siesta Key Beach, offering convenient access to local attractions including the John and Mable Ringling Museum of Art (18 km away).
The 116-square-metre property boasts two bedrooms, two bathrooms, and sleeps up to 11 guests, featuring a private pool, jacuzzi, sauna, and fitness centre, alongside free Wi-Fi and a fully equipped kitchen.
Book Me Baby! Esquina Paraiso On Siesta Key - Siesta Key, FL
10 11 reviews
Siesta Key, FL
12/07 – 19/07
231 €/nighttotal: 1617 € (7 )

Book Me Baby! Esquina Paraiso On Siesta Key

2 5
apartment , Siesta Key
This Siesta Key Anchorage condo, situated on the fifth floor near the south bridge and a short distance from Siesta Key Village, offers direct beach access across the street.
The 120 square metre (approximately 1292 square feet) apartment boasts three bedrooms, two bathrooms, sleeps six guests, and includes a private terrace, swimming pool access, and resort amenities such as tennis courts and a fitness centre.
Charming Siesta Key Condo With Private Beach Access - Siesta Key, FL
9.3 3 reviews
Siesta Key, FL
21/11 – 01/12
189 €/nighttotal: 1890 € (10 )

Charming Siesta Key Condo With Private Beach Access

1 2
house , Siesta Key
This Siesta Key apartment is located a short walk from Crescent Beach, 17.7 kilometres from the John and Mable Ringling Museum of Art and 19.3 kilometres from the Sarasota International Convention Centre.
This 89 square metre apartment accommodates up to seven guests and features private beach access, an outdoor swimming pool, a sauna, a fitness centre, a tennis court, and on-site parking.
Gertrude Siesta | Private Patios, Beach & Village, 100 Steps To Best Views On Siesta Key - Siesta Key, FL
9.7 168 reviews
Siesta Key, FL
04/07 – 08/07
938 €/nighttotal: 3752 € (4 )

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

3 4
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.

Best Siesta Key, FL holiday rentals with parking

Sea Club Ii Unit 2b By Prime Vacations - Siesta Key, FL
Siesta Key, FL
23/07 – 26/07
273 €/nighttotal: 819 € (3 )

Sea Club Ii Unit 2b By Prime Vacations

1 4
apartment , Siesta Key
Sea Club II Unit 2B by Prime Vacations is a flat located in Siesta Key, a 6-minute walk from Crescent Beach and 17 kilometres from The John and Mable Ringling Museum of Art.
This 48 square metre apartment accommodates up to 7 guests with one bedroom and one bathroom, offering air conditioning, complimentary Wi-Fi, and on-site parking, with Marina Jack Restaurant And Marina 7.3 kilometres away and Sarasota Opera 7.4 kilometres away.
Beautifully Updated Unit With Bay Views! - Harbor Towers- 417 - Siesta Key, FL
9.0 4 reviews
Siesta Key, FL
27/06 – 11/07
259 €/nighttotal: 3626 € (14 )

Beautifully Updated Unit With Bay Views! - Harbor Towers- 417

2 5
apartment , Siesta Key
This Siesta Key bayfront condo, situated directly on the Intracoastal Waterway and opposite Siesta Key Beach, offers stunning bay views and easy access to the Siesta Key Breeze Trolley.
The 107 square metre (1150 square feet) apartment features two bedrooms, two bathrooms, a fully equipped kitchen, and a screened lanai; sleeping up to six guests and including use of two community pools, three tennis courts, and a fitness centre within the Harbor Towers complex.
2bed/2bath Condo Next To Siesta Key ~A Hidden Gem - Siesta Key, FL
9.2 43 reviews
Siesta Key, FL
24/06 – 28/06
170 €/nighttotal: 680 € (4 )

2bed/2bath Condo Next To Siesta Key ~A Hidden Gem

2 2
house , Gulf Gate Estates
This two-bedroom Gulf Gate Estates condo is situated approximately 11-16km from Sarasota attractions such as the Ringling Museum and St. Armands Circle, and offers easy access to Siesta Key beach.
The property boasts a fully equipped kitchen, air conditioning, a swimming pool, private parking, and sleeps up to eight guests, providing comfortable accommodation near Gulf Gate Estates.
Charming Two Bedroom Condo With Pool View Siesta Key Bay Oaks - Siesta Key, FL
8.3 3 reviews
Siesta Key, FL
04/07 – 08/07
322 €/nighttotal: 1288 € (4 )

Charming Two Bedroom Condo With Pool View Siesta Key Bay Oaks

3 4
apartment , Siesta Key
This Siesta Key apartment, a four-minute walk from Crescent Beach and 18 kilometres from the Ringling Museum of Art, offers easy access to Sarasota's attractions.
The 102-square-metre self-catering property sleeps fifteen guests, features three bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, free Wi-Fi, on-site parking, and boasts a pool view.
©2026 cozycozy.com