Vacation homes Siesta Key
Siesta Key
2 guests

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2

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Siesta Key

Jun 03 - Jun 04 ·
2 guests

Vacation homes in Siesta Key

Siesta Key
2 guests

Adults:

2

Children:

0

Child’s age:

Over 970 stays assessed to highlight the standout picks
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Navigation

1. Bianco Sands By Beachside Management

2. Siesta Key Beach House

3. Crescent Beach Villas By Beachside Management

4. Sun And Sea By Beachside Management

5. Beautiful Property On Siesta Key

6. Siesta Villa Laughing Gull

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

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

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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

Featuring parking, the welcoming Bianco Sands By Beachside Management Siesta Key villa is located 2.9 km from the Siesta Key Drum Circle.

The presence of a plunge swimming pool, a plunge pool ensures a relaxing stay.

8.8
102 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

Featuring parking, the welcoming Bianco Sands By Beachside Management Siesta Key villa is located 2.9 km from the Siesta Key Drum Circle.

The presence of a plunge swimming pool, a plunge pool ensures a relaxing stay.

8.8
102 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

Located just 1.7 km from the Siesta Key Marina, the 2-bedroom Siesta Key Beach House villa offers a terrace with views of the sea. Guests can relax by a swimming pool and enjoy the proximity to the Jamaica Royale, which is only a 9-minute walk away.

At the accommodation, windsurfing, canoeing, and fishing can be arranged upon request.

8.4
67 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

Located just 1.7 km from the Siesta Key Marina, the 2-bedroom Siesta Key Beach House villa offers a terrace with views of the sea. Guests can relax by a swimming pool and enjoy the proximity to the Jamaica Royale, which is only a 9-minute walk away.

At the accommodation, windsurfing, canoeing, and fishing can be arranged upon request.

8.4
67 reviews
From US$ 237 / 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

The welcoming Crescent Beach Villas By Beachside Management Siesta Key is located 4.3 km from the Grand Canal, giving access to various tourist spots nearby.

Offering a plunge swimming pool, this accommodation also features a plunge pool for a complete relaxation.

8.2
26 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

The welcoming Crescent Beach Villas By Beachside Management Siesta Key is located 4.3 km from the Grand Canal, giving access to various tourist spots nearby.

Offering a plunge swimming pool, this accommodation also features a plunge pool for a complete relaxation.

8.2
26 reviews
From US$ 253 / 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

Situated approximately a 5-minute walk from Green Turtle Shell & Gift City, Sun And Sea By Beachside Management Siesta Key villa offers quick access to numerous city landmarks nearby.

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

Situated approximately a 5-minute walk from Green Turtle Shell & Gift City, Sun And Sea By Beachside Management Siesta Key villa offers quick access to numerous city landmarks nearby.

8.8
26 reviews
From US$ 213 / night
  • 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 mere 12 minutes' walk from the Crescent Arms, the 1-bedroom Beautiful Property On Siesta Key villa comes with a private swimming pool equipped with sun loungers.

The area is popular for those who like windsurfing, canoeing, and fishing.

7.8
58 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 mere 12 minutes' walk from the Crescent Arms, the 1-bedroom Beautiful Property On Siesta Key villa comes with a private swimming pool equipped with sun loungers.

The area is popular for those who like windsurfing, canoeing, and fishing.

7.8
58 reviews
From US$ 200 / 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

Situated only 6 minutes' walk from Siesta Harbour Condominium, the 2-bedroom Siesta Villa Laughing Gull Siesta Key provides access to numerous tourist attractions in the area.

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

Situated only 6 minutes' walk from Siesta Harbour Condominium, the 2-bedroom Siesta Villa Laughing Gull Siesta Key provides access to numerous tourist attractions in the area.

7.5
2 reviews
From US$ 493 / night
  • 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

Featuring a private swimming pool for guests' relaxation, the 2-bedroom Pool Villa Happy Dolphin 10 Min Walk To Siesta Beach Siesta Key is located just 1.6 km from the Jamaica Royale. Featuring access to a terrace, this Siesta Key villa is located approximately a 10-minute drive from the Big Sarasota Pass.

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

Featuring a private swimming pool for guests' relaxation, the 2-bedroom Pool Villa Happy Dolphin 10 Min Walk To Siesta Beach Siesta Key is located just 1.6 km from the Jamaica Royale. Featuring access to a terrace, this Siesta Key villa is located approximately a 10-minute drive from the Big Sarasota Pass.

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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

Situated 7 minutes' walk from Siesta Harbour Condominium, Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities Siesta Key provides access to numerous tourist attractions in the area.

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

Situated 7 minutes' walk from Siesta Harbour Condominium, Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities Siesta Key provides access to numerous tourist attractions in the area.

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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 only a 7-minute walk from the Siesta Key Marina, Exclusive 5 Star Condo With Balcony On Siesta Key Sarasota County Condo 1004 villa provides an outdoor swimming pool, a sauna for additional comfort. Featuring private car parking, the villa is located 2.3 km from the Siesta Key Beach.

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 only a 7-minute walk from the Siesta Key Marina, Exclusive 5 Star Condo With Balcony On Siesta Key Sarasota County Condo 1004 villa provides an outdoor swimming pool, a sauna for additional comfort. Featuring private car parking, the villa is located 2.3 km from the Siesta Key Beach.

  • Private beach
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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
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Heated swimming pool

Located within 10 minutes' drive of the Bay Island, the 2-bedroom Private Village Home With Heated Pool & Spa With Private Front Courtyard Siesta Key provides access to a private swimming pool. Featuring a Jacuzzi, the Siesta Key villa is nestled 3.3 km from the shaped Crescent Beach.

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

2.0 km (1.3 mi) from city center
158
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Heated swimming pool

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

Located within 10 minutes' drive of the Bay Island, the 2-bedroom Private Village Home With Heated Pool & Spa With Private Front Courtyard Siesta Key provides access to a private swimming pool. Featuring a Jacuzzi, the Siesta Key villa is nestled 3.3 km from the shaped Crescent Beach.

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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

The 1-bedroom Village West In Heart Of Siesta Siesta Key villa offers quick access to such city attractions as the Siesta Key Craft Festival, located approximately 5 minutes' walk away.

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

The 1-bedroom Village West In Heart Of Siesta Siesta Key villa offers quick access to such city attractions as the Siesta Key Craft Festival, located approximately 5 minutes' walk away.

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Three Sandy Sisters

6005 Midnight Pass Rd #N8
0.8 km (0.5 mi) from city center
137
  • Cookware/ Kitchen utensils
  • Ironing facilities
  • Tea and coffee facilities
  • Heating
  • Golf centre
  • Golf course

Located merely 1.4 km from the Siesta Beach Pavillion, Three Sandy Sisters Siesta Key villa provides access to various tourist attractions in the vicinity.

Three Sandy Sisters

0.8 km (0.5 mi) from city center
137
  • Cookware/ Kitchen utensils
  • Ironing facilities
  • Tea and coffee facilities
  • Heating
  • Golf centre
  • Golf course

Three Sandy Sisters

Located merely 1.4 km from the Siesta Beach Pavillion, Three Sandy Sisters Siesta Key villa provides access to various tourist attractions in the vicinity.

Vacation homes near Siesta Key

These options match your search but are within a one-hour drive of the city (up to 80 km / 50 mi).

  • Best-rated
  • Beach access
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Siesta Key Beachside Villas

124 Columbus Blvd
2.2 km (1.3 mi) from Siesta Key
  • BBQ facilities
  • Car park
    US$ 10 per day
  • Housekeeping
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

The self-catering Siesta Key Beachside Villas Sarasota is located a 5-minute walk from the Siesta Key Beach Access 2 and offers guests to enjoy cycling.

This Sarasota property includes leisure amenities, like a picnic area and barbecue grills, as well as a swimming pool.

8.8
356 reviews
~ US$223 / night

Siesta Key Beachside Villas

2.2 km (1.3 mi) from Siesta Key
  • BBQ facilities
  • Car park
    US$ 10 per day
  • Housekeeping
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

Siesta Key Beachside Villas

The self-catering Siesta Key Beachside Villas Sarasota is located a 5-minute walk from the Siesta Key Beach Access 2 and offers guests to enjoy cycling.

This Sarasota property includes leisure amenities, like a picnic area and barbecue grills, as well as a swimming pool.

8.8
356 reviews
From US$ 223 / 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

Positioned approximately a 25-minute walk from bustling shopping destinations such as the Shell Point Cottage, Pirates Pointe Resort Ruskin villa offers guests to use a free private car park. The property features opportunities for canoeing and fishing in the area, about 5 km from Ott's Off Leash Dog Sanctuary Park.

The Ruskin accommodation has a swimming pool and a patio with outdoor dining areas for more comfort.

9.4
90 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

Positioned approximately a 25-minute walk from bustling shopping destinations such as the Shell Point Cottage, Pirates Pointe Resort Ruskin villa offers guests to use a free private car park. The property features opportunities for canoeing and fishing in the area, about 5 km from Ott's Off Leash Dog Sanctuary Park.

The Ruskin accommodation has a swimming pool and a patio with outdoor dining areas for more comfort.

9.4
90 reviews
From US$ 169 / night
  • Private beach
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Sand Glo Villas

19316 Gulf Boulevard
70.9 km (44.1 mi) from Siesta Key
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Flat-screen TV
  • Tennis court
  • Sun loungers

Staying at the 6-room Sand Glo Villas Clearwater Beach, guests can easily reach the Seminole City Park, located approximately 10 minutes' drive away.

There is canoeing, tennis, and fishing available on-site.

9.7
88 reviews
~ US$161 / night

Sand Glo Villas

70.9 km (44.1 mi) from Siesta Key
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Flat-screen TV
  • Tennis court
  • Sun loungers

Sand Glo Villas

Staying at the 6-room Sand Glo Villas Clearwater Beach, guests can easily reach the Seminole City Park, located approximately 10 minutes' drive away.

There is canoeing, tennis, and fishing available on-site.

9.7
88 reviews
From US$ 161 / night
  • Guest favorite
  • 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

Siesta Key Beach Resort And Suites Sarasota villa is situated only an 8-minute walk from the Siesta Key Beach Access 2 and features spa therapy, a shared lounge, and various recreational opportunities for a delightful stay.

The presence of a swimming pool, along with a hot tub, ensures complete relaxation after a busy day. Activities in the area include cycling.

8.7
543 reviews
~ US$273 / 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

Siesta Key Beach Resort And Suites Sarasota villa is situated only an 8-minute walk from the Siesta Key Beach Access 2 and features spa therapy, a shared lounge, and various recreational opportunities for a delightful stay.

The presence of a swimming pool, along with a hot tub, ensures complete relaxation after a busy day. Activities in the area include cycling.

8.7
543 reviews
From US$ 273 / night
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Gorgeous Waterfront! Mermaid'S Retreat Wows!

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

Offering Wi-Fi, Gorgeous Waterfront! Mermaid'S Retreat Wows! Englewood villa is located about a 25-minute walk from the Peninsula at Englewood Beach.

9.7
22 reviews
~ US$307 / night

Gorgeous Waterfront! Mermaid'S Retreat Wows!

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

Gorgeous Waterfront! Mermaid'S Retreat Wows!

Offering Wi-Fi, Gorgeous Waterfront! Mermaid'S Retreat Wows! Englewood villa is located about a 25-minute walk from the Peninsula at Englewood Beach.

9.7
22 reviews
From US$ 307 / night

Are you in a hurry?

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

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

8.8 / 10

(102 Reviews)

From 141$
Siesta Key Beach House

8.4 / 10

(67 Reviews)

From 237$
Crescent Beach Villas By Beachside Management

8.2 / 10

(26 Reviews)

From 253$
Sun And Sea By Beachside Management

8.8 / 10

(26 Reviews)

From 213$
Beautiful Property On Siesta Key

7.8 / 10

(58 Reviews)

From 200$

More accommodations in Siesta Key

Beachpoint Cottages Beachpoint Cottages Beachpoint Cottages
9.1
215 reviews
~ US$ 279 / night
Siesta Key Bungalows Siesta Key Bungalows Siesta Key Bungalows
8.4
336 reviews
~ US$ 199 / night
Living The Dream By Beachside Management Living The Dream By Beachside Management Living The Dream By Beachside Management
9.3
21 reviews
~ US$ 234 / night
The Ringling Beach House The Ringling Beach House The Ringling Beach House
8.3
461 reviews
~ US$ 582 / night
Sun And Sea By Beachside Management Sun And Sea By Beachside Management Sun And Sea By Beachside Management
8.8
26 reviews
~ US$ 213 / night

Frequently Asked Questions

What vacation homes in Siesta Key have great access to the beach?

Siesta Key Beachside Villas and Pirates Pointe Resort are both just a short walk to the beach, offering easy beach access. These locations let you enjoy the sand and surf at any time.

Tip:

Arrive before 10am to find better parking spots at the beach accesses.

Which vacation homes in Siesta Key are ideal for families?

Bianco Sands By Beachside Management and Sun And Sea By Beachside Management cater well to families, providing spacious accommodations and family-friendly activities. They are close to parks and local attractions.

Tip:

Book during the off-peak season in late August for lower rates and fewer crowds.

Are there vacation homes in Siesta Key with pools?

The Stay At Sarasota County Villa offers a relaxing pool experience and is suitable for families looking to unwind. You can also enjoy a pool at the Private Village Home with Heated Pool & Spa.

Tip:

Visit the pool during weekdays for a quieter atmosphere without weekend crowds.

Which vacation homes near Siesta Key are suitable for couples?

The Gorgeous Waterfront! Mermaid'S Retreat and the exclusive Siesta Villa Laughing Gull are both excellent choices for couples, providing stunning views and a romantic atmosphere.

Tip:

Consider booking a sunset dinner at a nearby restaurant while enjoying the water views.

Are there vacation homes in Siesta Key with views?

Crescent Beach Villas By Beachside Management features breathtaking views of the Gulf, making it perfect for a relaxing stay. The views enhance the overall experience of Siesta Key's natural beauty.

Tip:

Request a room on a higher floor to maximize your view of the beach and sunset.

Which budget-friendly vacation homes in Siesta Key are recommended?

Bianco Sands By Beachside Management and Sand Glo Villas provide comfortable stays without breaking the bank. These options are close to attractions and offer a good balance of price and comfort.

Tip:

Look for last-minute deals online for additional savings, especially during the off-season.

Where can I find two-bedroom vacation homes in Siesta Key?

The Siesta Key Beach House and the Village West In Heart Of Siesta offer spacious two-bedroom options, perfect for small families or groups. They are conveniently located near activities and the beach.

Tip:

Book early to secure a two-bedroom home during peak season, from December to April.

What unique activities should I try while staying in Siesta Key?

Visit the Drum Circle at Siesta Key Beach every Sunday to experience live music and a local vibe. It's a fun way to meet locals and enjoy beach culture.

Tip:

Arrive by 5pm for the best location to watch the sunset during the Drum Circle.

How can I get to Siesta Key from the nearest airport?

Sarasota-Bradenton International Airport is about 12 miles away, with taxi and shuttle services readily available. Renting a car is also an option for more freedom during your stay.

Tip:

Consider scheduling your airport pickup during off-peak hours to avoid traffic delays.

What local foods should I try while on Siesta Key?

Don't miss fresh seafood, especially the iconic grouper sandwich found at local restaurants like The Cottage. Enjoying these dishes will give you a real taste of Florida.

Tip:

Try The Cottage for breakfast or lunch to taste their famous key lime pie - a local favorite.

Siesta Key and related destinations

Location