Siesta Key
2 guests

Adults:

2

Children:

0

Child’s age:

Siesta Key

Sep 19 - Sep 20 ·
2 guests

Siesta Key Vacation Rentals

Siesta Key
2 guests

Adults:

2

Children:

0

Child’s age:

Over 1,160 stays assessed to highlight the standout picks

Navigation

1. Bianco Sands By Beachside Management

2. Siesta Key Beach House

3. Sun And Sea By Beachside Management

4. Beautiful Property On Siesta Key

Cheap Siesta Key Vacation Rentals

5. Crescent Beach Villas By Beachside Management

6. Siesta Villa Laughing Gull

7. Pool Villa Happy Dolphin 10 Min Walk To Siesta Beach

Pet Friendly Vacation Rentals Siesta Key Florida

8. Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities

9. Exclusive 5 Star Condo With Balcony On Siesta Key Sarasota County Condo 1004

10. Private Village Home With Heated Pool & Spa With Private Front Courtyard

Siesta Key Luxury Vacation Rentals

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Bianco Sands By Beachside Management

1126 Point Of Rocks Road
2.7 km (1.7 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities

Located around a 10-minute ride from Edson Keith Estate Park, the 9-room Bianco Sands By Beachside Management Siesta Key villa provides access to a plunge pool. Featuring a plunge pool, this Siesta Key villa is nestled 4.2 km from the Grand Canal.

8.9
83 reviews
~ US$141 / night

Bianco Sands By Beachside Management

2.7 km (1.7 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities

Bianco Sands By Beachside Management

Located around a 10-minute ride from Edson Keith Estate Park, the 9-room Bianco Sands By Beachside Management Siesta Key villa provides access to a plunge pool. Featuring a plunge pool, this Siesta Key villa is nestled 4.2 km from the Grand Canal.

8.9
83 reviews
From US$ 141 / night
  • Private beach
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Siesta Key Beach House

1232 Derby Lane
0.9 km (0.6 mi) from city center
131
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf centre
  • Heated swimming pool

Situated approximately a 20-minute walk from the Siesta Key Beach, the 3-bedroom Siesta Key Beach House villa provides access to numerous tourist attractions in the area. This property welcomes up to 6 guests and provides karaoke to entertain them.

An array of activities such as windsurfing, canoeing, and fishing can be enjoyed on-site.

8.4
74 reviews
~ US$237 / night

Siesta Key Beach House

0.9 km (0.6 mi) from city center
131
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf centre
  • Heated swimming pool

Siesta Key Beach House

Situated approximately a 20-minute walk from the Siesta Key Beach, the 3-bedroom Siesta Key Beach House villa provides access to numerous tourist attractions in the area. This property welcomes up to 6 guests and provides karaoke to entertain them.

An array of activities such as windsurfing, canoeing, and fishing can be enjoyed on-site.

8.4
74 reviews
From US$ 237 / night
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Sun And Sea By Beachside Management

1135 Sun N Sea Drive Unit 1 & 2
2.3 km (1.4 mi) from city center
  • Cookware/ Kitchen utensils
  • Ironing facilities
  • Tea and coffee facilities

Sun And Sea By Beachside Management Siesta Key villa enjoys its location 1 km from Crescent Beach and overlooks the garden.

8.8
26 reviews
~ US$213 / night

Sun And Sea By Beachside Management

2.3 km (1.4 mi) from city center
  • Cookware/ Kitchen utensils
  • Ironing facilities
  • Tea and coffee facilities

Sun And Sea By Beachside Management

Sun And Sea By Beachside Management Siesta Key villa enjoys its location 1 km from Crescent Beach and overlooks the garden.

8.8
26 reviews
From US$ 213 / night

Cheap Siesta Key Vacation Rentals

  • Private beach
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Beautiful Property On Siesta Key

1234 Derby Lane
0.9 km (0.6 mi) from city center
100
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf centre
  • Heated swimming pool

Located a 25-minute walk from the Siesta Key Village, Beautiful Property On Siesta Key villa offers karaoke for guests' leisure. Guests of the 2-bedroom villa, situated in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida can also enjoy private car parking on site.

Active guests will appreciate windsurfing, canoeing, and fishing available to diversify their stay.

8.3
62 reviews
~ US$200 / night

Beautiful Property On Siesta Key

0.9 km (0.6 mi) from city center
100
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf centre
  • Heated swimming pool

Beautiful Property On Siesta Key

Located a 25-minute walk from the Siesta Key Village, Beautiful Property On Siesta Key villa offers karaoke for guests' leisure. Guests of the 2-bedroom villa, situated in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida can also enjoy private car parking on site.

Active guests will appreciate windsurfing, canoeing, and fishing available to diversify their stay.

8.3
62 reviews
From US$ 200 / night
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Crescent Beach Villas By Beachside Management

1126 Crescent Street
2.7 km (1.7 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities

Situated around 25 minutes on foot from the Jamaica Royale, Crescent Beach Villas By Beachside Management Siesta Key includes a plunge swimming pool, as well as a plunge pool to relax in. Offering a prime location in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida, the welcoming villa features Wi-Fi and parking.

8.2
23 reviews
~ US$253 / night

Crescent Beach Villas By Beachside Management

2.7 km (1.7 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities

Crescent Beach Villas By Beachside Management

Situated around 25 minutes on foot from the Jamaica Royale, Crescent Beach Villas By Beachside Management Siesta Key includes a plunge swimming pool, as well as a plunge pool to relax in. Offering a prime location in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida, the welcoming villa features Wi-Fi and parking.

8.2
23 reviews
From US$ 253 / night
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Siesta Villa Laughing Gull

1272 Moonmist Circle
1.3 km (0.8 mi) from city center
84
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Terrace

Located just a 6-minute walk from the Crescent Arms, the 2-bedroom Siesta Villa Laughing Gull Siesta Key boasts a heated pool and can accommodate up to 5.

7.5
2 reviews
~ US$493 / night

Siesta Villa Laughing Gull

1.3 km (0.8 mi) from city center
84
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Terrace

Siesta Villa Laughing Gull

Located just a 6-minute walk from the Crescent Arms, the 2-bedroom Siesta Villa Laughing Gull Siesta Key boasts a heated pool and can accommodate up to 5.

7.5
2 reviews
From US$ 493 / night

Pet Friendly Vacation Rentals Siesta Key Florida

  • Great deal
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Pool Villa Happy Dolphin 10 Min Walk To Siesta Beach

5584 Shadow Lawn Drive
0.3 km (0.2 mi) from city center
156
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Heated swimming pool
  • Outdoor swimming pool

Located only 5 minutes' walk from the Siesta Key Village, the 2-bedroom Pool Villa Happy Dolphin 10 Min Walk To Siesta Beach Siesta Key features a year-round outdoor swimming pool and can accommodate up to 4 guests.

Pool Villa Happy Dolphin 10 Min Walk To Siesta Beach

0.3 km (0.2 mi) from city center
156
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Heated swimming pool
  • Outdoor swimming pool

Pool Villa Happy Dolphin 10 Min Walk To Siesta Beach

Located only 5 minutes' walk from the Siesta Key Village, the 2-bedroom Pool Villa Happy Dolphin 10 Min Walk To Siesta Beach Siesta Key features a year-round outdoor swimming pool and can accommodate up to 4 guests.

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Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities

6415 Midnight Pass Rd
1.9 km (1.2 mi) from city center
1000
  • Valet parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Heating
  • Fitness centre

The 2-bedroom Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities Siesta Key offers proximity to nearby tourist spots, such as Siesta Harbour Condominium, situated merely 550 metres away. Offering a spa salon, this accommodation can accommodate up to 4 guests.

Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities

1.9 km (1.2 mi) from city center
1000
  • Valet parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Heating
  • Fitness centre

Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities

The 2-bedroom Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities Siesta Key offers proximity to nearby tourist spots, such as Siesta Harbour Condominium, situated merely 550 metres away. Offering a spa salon, this accommodation can accommodate up to 4 guests.

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Exclusive 5 Star Condo With Balcony On Siesta Key Sarasota County Condo 1004

6415 Midnight Pass Rd
1.9 km (1.2 mi) from city center
1000
  • Valet parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Sauna
  • Outdoor swimming pool

Located around a 5-minute ride from the Siesta Key Marina, the 1-bedroom Exclusive 5 Star Condo With Balcony On Siesta Key Sarasota County Condo 1004 villa offers an outdoor swimming pool, a sauna for a truly relaxing stay. Hosting up to 6 guests, the Siesta Key villa offers a prime location in the vicinity of Green Turtle Shell & Gift City.

Exclusive 5 Star Condo With Balcony On Siesta Key Sarasota County Condo 1004

1.9 km (1.2 mi) from city center
1000
  • Valet parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Sauna
  • Outdoor swimming pool

Exclusive 5 Star Condo With Balcony On Siesta Key Sarasota County Condo 1004

Located around a 5-minute ride from the Siesta Key Marina, the 1-bedroom Exclusive 5 Star Condo With Balcony On Siesta Key Sarasota County Condo 1004 villa offers an outdoor swimming pool, a sauna for a truly relaxing stay. Hosting up to 6 guests, the Siesta Key villa offers a prime location in the vicinity of Green Turtle Shell & Gift City.

Siesta Key Vacation Rentals Oceanfront

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Private Village Home With Heated Pool & Spa With Private Front Courtyard

327 Avenida Milano
2.0 km (1.3 mi) from city center
158
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

Hosting up to 6 guests, the 3-bedroom Private Village Home With Heated Pool & Spa With Private Front Courtyard Siesta Key is nestled in a beach area, around 4 km from Coolidge Park. The villa offers guests a relaxing experience with a Jacuzzi.

Private Village Home With Heated Pool & Spa With Private Front Courtyard

2.0 km (1.3 mi) from city center
158
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

Private Village Home With Heated Pool & Spa With Private Front Courtyard

Hosting up to 6 guests, the 3-bedroom Private Village Home With Heated Pool & Spa With Private Front Courtyard Siesta Key is nestled in a beach area, around 4 km from Coolidge Park. The villa offers guests a relaxing experience with a Jacuzzi.

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Village West In Heart Of Siesta

5216 Avenida Navarra
2.1 km (1.3 mi) from city center
54
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Outdoor swimming pool

Featuring an outdoor swimming pool for guests' relaxation, the 1-bedroom Village West In Heart Of Siesta Siesta Key villa is located only 550 metres from Siesta Key Beach Access #5. The property can host up to 4 guests and offers quick access to the co-op Gallery on Siesta Key, located just a 5-minute walk away.

10
1 reviews

Village West In Heart Of Siesta

2.1 km (1.3 mi) from city center
54
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Outdoor swimming pool

Village West In Heart Of Siesta

Featuring an outdoor swimming pool for guests' relaxation, the 1-bedroom Village West In Heart Of Siesta Siesta Key villa is located only 550 metres from Siesta Key Beach Access #5. The property can host up to 4 guests and offers quick access to the co-op Gallery on Siesta Key, located just a 5-minute walk away.

10
1 reviews
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Three Sandy Sisters

6005 Midnight Pass Rd #N8
0.8 km (0.5 mi) from city center
137
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Golf centre
  • Golf course

Situated only 0.6 km from the Jamaica Royale, the 2-bedroom Three Sandy Sisters Siesta Key villa is ideal for up to 6 guests. Guests can enjoy fishing at the villa, located around a 20-minute walk from the Siesta Key Beach.

Three Sandy Sisters

0.8 km (0.5 mi) from city center
137
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Golf centre
  • Golf course

Three Sandy Sisters

Situated only 0.6 km from the Jamaica Royale, the 2-bedroom Three Sandy Sisters Siesta Key villa is ideal for up to 6 guests. Guests can enjoy fishing at the villa, located around a 20-minute walk from the Siesta Key Beach.

Vacation rentals near Siesta Key

Siesta Key Vacation Rentals with Private Pool

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Sand Glo Villas

19316 Gulf Boulevard
70.9 km (44.1 mi) from Siesta Key
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Sand Glo Villas Clearwater Beach provides easy access to various city attractions, such as Smugglers Cove Adventure Golf, situated approximately 5 minutes' walk away.

The surroundings feature canoeing, tennis, and fishing.

9.7
79 reviews
~ US$161 / night

Sand Glo Villas

70.9 km (44.1 mi) from Siesta Key
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Sand Glo Villas

Sand Glo Villas Clearwater Beach provides easy access to various city attractions, such as Smugglers Cove Adventure Golf, situated approximately 5 minutes' walk away.

The surroundings feature canoeing, tennis, and fishing.

9.7
79 reviews
From US$ 161 / night
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Pirates Pointe Resort

1800 Kofresi Court
50.9 km (31.6 mi) from Siesta Key
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Heated swimming pool

Pirates Pointe Resort Ruskin villa enjoys a convenient location in Ruskin and offers its guests to make use of a swimming pool.

In this local area canoeing and fishing and other outdoor activities are available.

9.5
80 reviews
~ US$169 / night

Pirates Pointe Resort

50.9 km (31.6 mi) from Siesta Key
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Heated swimming pool

Pirates Pointe Resort

Pirates Pointe Resort Ruskin villa enjoys a convenient location in Ruskin and offers its guests to make use of a swimming pool.

In this local area canoeing and fishing and other outdoor activities are available.

9.5
80 reviews
From US$ 169 / night
  • Best-rated
  • Beach access
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Siesta Key Beach Resort And Suites

5311 Ocean Boulevard
1.9 km (1.2 mi) from Siesta Key
  • Cookware/ Kitchen utensils
  • Car park
    US$ 10 per day
  • Security
  • Air conditioning
  • Live entertainment
  • Heated swimming pool

Located a mere 650 metres from the Siesta Key Beach Access 2, Siesta Key Beach Resort And Suites Sarasota villa provides a swimming pool, a Jacuzzi for a more relaxing experience. This Sarasota resort is located in close proximity to the Seaside Vacation Villas, offering spa therapy, a shared lounge, and various recreational opportunities for a delightful experience.

Bicycles for hire are available at the Sarasota accommodation, while cycling can also be arranged onsite.

8.8
480 reviews
~ US$235 / night

Siesta Key Beach Resort And Suites

1.9 km (1.2 mi) from Siesta Key
  • Cookware/ Kitchen utensils
  • Car park
    US$ 10 per day
  • Security
  • Air conditioning
  • Live entertainment
  • Heated swimming pool

Siesta Key Beach Resort And Suites

Located a mere 650 metres from the Siesta Key Beach Access 2, Siesta Key Beach Resort And Suites Sarasota villa provides a swimming pool, a Jacuzzi for a more relaxing experience. This Sarasota resort is located in close proximity to the Seaside Vacation Villas, offering spa therapy, a shared lounge, and various recreational opportunities for a delightful experience.

Bicycles for hire are available at the Sarasota accommodation, while cycling can also be arranged onsite.

8.8
480 reviews
From US$ 235 / night
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Waterfront Mermaids Retreat Charms! Pool & Bay

5075 North Beach Road, E, Englewood Florida 34285
39.7 km (24.7 mi) from Siesta Key
51
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Outdoor swimming pool

Featuring a year-round outdoor swimming pool for guests' relaxation, the 1-bedroom Waterfront Mermaids Retreat Charms! Pool & Bay Englewood villa is located about a 10-minute ride from Cedar Point Environmental Park. Featuring sea views, the Englewood villa invites guests to visit the Lemon Bay Aquatic Preserve, located 4.3 km away.

9.4
24 reviews
~ US$307 / night

Waterfront Mermaids Retreat Charms! Pool & Bay

39.7 km (24.7 mi) from Siesta Key
51
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Outdoor swimming pool

Waterfront Mermaids Retreat Charms! Pool & Bay

Featuring a year-round outdoor swimming pool for guests' relaxation, the 1-bedroom Waterfront Mermaids Retreat Charms! Pool & Bay Englewood villa is located about a 10-minute ride from Cedar Point Environmental Park. Featuring sea views, the Englewood villa invites guests to visit the Lemon Bay Aquatic Preserve, located 4.3 km away.

9.4
24 reviews
From US$ 307 / night

Are you in a hurry?

Here is a quick list of Vacation Rentals in Siesta Key, selected based on their rating

Name of hotel Accommodation Rating Price, $
Bianco Sands By Beachside Management

8.9 / 10

(83 Reviews)

From 141$
Siesta Key Beach House

8.4 / 10

(74 Reviews)

From 237$
Sun And Sea By Beachside Management

8.8 / 10

(26 Reviews)

From 213$
Beautiful Property On Siesta Key

8.3 / 10

(62 Reviews)

From 200$
Crescent Beach Villas By Beachside Management

8.2 / 10

(23 Reviews)

From 253$

Siesta Key and related destinations

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