Siesta Key Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Siesta Key, Florida, USA

New Steps to the ⭐ Beach, Short Walk to the Village
9.8 (48 Reviews)
2 Bedrooms 4 Guests
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10.0 (8 Reviews)
2 Bedrooms 4 Guests
From GB £250 per night
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10.0 (183 Reviews)
1 Bedroom 2 Guests
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10.0 (6 Reviews)
6 Bedrooms 6 Guests
From GB £292 per night
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10.0 (6 Reviews)
1 Bedroom 2 Guests
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10.0 (4 Reviews)
2 Bedrooms 6 Guests
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10.0 (5 Reviews)
1 Bedroom 2 Guests
New A Great Day At The Beach! - Aloha Kai #6 - Roelens
From GB £1,912 per night
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10.0 (3 Reviews)
5 Bedrooms 13 Guests
From GB £889 per night
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10.0 (3 Reviews)
3 Bedrooms 10 Guests
From GB £393 per night
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10.0 (3 Reviews)
1 Bedroom 8 Guests
From GB £359 per night
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10.0 (3 Reviews)
3 Bedrooms 8 Guests
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10.0 (3 Reviews)
3 Bedrooms 6 Guests
From GB £1,324 per night
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10.0 (2 Reviews)
3 Bedrooms 8 Guests
From GB £1,307 per night
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10.0 (2 Reviews)
4 Bedrooms 14 Guests
From GB £765 per night
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10.0 (2 Reviews)
4 Bedrooms 8 Guests
New CA 501S Barbs Beach getaway siesta key FL
New
2 Bedrooms 4 Guests
From GB £692 per night
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10.0 (2 Reviews)
3 Bedrooms 8 Guests
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10.0 (2 Reviews)
2 Bedrooms 5 Guests
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10.0 (2 Reviews)
2 Bedrooms 6 Guests
New 2 bedroom 2 bath condo w/Screened in lanai
New
2 Bedrooms 4 Guests
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10.0 (2 Reviews)
2 Bedrooms 6 Guests
New Cozy Home Near the Beach - Aloha Kai #37 - Roelens
From GB £229 per night
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10.0 (2 Reviews)
1 Bedroom 4 Guests
New Tortuga – 2BR on Beach, Heated Pool & Sauna
New
2 Bedrooms 6 Guests
From GB £159 per night
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10.0 (2 Reviews)
2 Bedrooms 6 Guests
New Beachside Bliss Awaits - Aloha Kai #55- Roelens
New
1 Bedroom 4 Guests
New Beach Getaway! - Aloha Kai #42 - Roelens
New
1 Bedroom 4 Guests
New Harbor Towers 1BD with washer & dryer in unit!
New
1 Bedroom 2 Guests
New Studio on the Beach! - Aloha Kai #19 - Roelens
New
1 Bedroom 2 Guests
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10.0 (4 Reviews)
1 Bedroom 2 Guests
10.0 (102 Reviews)
2 Bedrooms 6 Guests
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
From GB £1,402 per night
10.0 (2 Reviews)
1 Bedroom 19 Guests
|
10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (100 Reviews)
2 Bedrooms 6 Guests
From GB £2,752 per night
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10.0 (1 Review)
8 Bedrooms 26 Guests
From GB £1,649 per night
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10.0 (1 Review)
8 Bedrooms 24 Guests
10.0 (99 Reviews)
2 Bedrooms 5 Guests
From GB £1,588 per night
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10.0 (1 Review)
4 Bedrooms 12 Guests
From GB £1,187 per night
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10.0 (1 Review)
4 Bedrooms 10 Guests
10.0 (97 Reviews)
2 Bedrooms 4 Guests
From GB £1,035 per night
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10.0 (1 Review)
4 Bedrooms 8 Guests
10.0 (94 Reviews)
2 Bedrooms 6 Guests
From GB £925 per night
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10.0 (1 Review)
3 Bedrooms 14 Guests
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10.0 (1 Review)
6 Bedrooms 14 Guests
10.0 (92 Reviews)
2 Bedrooms 4 Guests
From GB £801 per night
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10.0 (1 Review)
4 Bedrooms 10 Guests
10.0 (91 Reviews)
2 Bedrooms 5 Guests
From GB £782 per night
|
10.0 (1 Review)
3 Bedrooms 8 Guests

About Siesta Key Vacation Rentals

With more than 5372 Siesta Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Siesta Key.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Siesta Key, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Siesta Key. Places to stay near Siesta Key are 969.67 ft² on average, with prices averaging GB £366 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Siesta Key with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Siesta Key?

What are the top vacation rentals in Siesta Key?

How many Rentbyowner vacation rentals are available in Siesta Key?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 5372 in the Siesta Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Siesta Key. 

Nearby Neighborhood (4)

Neighborhood Property Count
Siesta Key Village Vacation Rentals in Sarasota, Florida 3919
Aloha Kai Vacation Rentals in Sarasota, Florida 129
South Sarasota Vacation Rentals in Sarasota, Florida 116
Bay Isle Vacation Rentals in Sarasota, Florida 39