Siesta Key Vacation Rentals

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Featured
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Beach, Bay, Food, Fun - 2BD/2BA
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Beach, Bay, Food, Fun - 2BD/2BA

2 Bedrooms
2 Bathrooms
4.67IconIconIconIconIcon
9 reviews
$174 - $250 / night
(excl. fees & taxes)
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2 Bedroom/2 Bath, One Floor condominium
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Come enjoy all of Sarasota and Siesta Key amenities without the congestion and just minutes to Siesta Key Beach.

2 Bedrooms
2 Bathrooms
$100 / night
(excl. fees & taxes)
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#1 Siesta Key Beach, Pool GlassHouse
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(3) E-Z Payments, beach supply & more

2 Bedrooms
2 Bathrooms
4.57IconIconIconIconIcon
49 reviews
$235 / night
(excl. fees & taxes)
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Gulf Gate Escapes near Siesta Key beaches
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Close to the beach/ pet sitting is available / hot tub/ garden

1 Bedroom
1 Bathroom
4.91IconIconIconIconIcon
90 reviews
$129 / night
(excl. fees & taxes)
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Siesta Key Beachfront Condo
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The closest condo to the Gulf of Mexico on Siesta Key

2 Bedrooms
2 Bathrooms
$129 / night
(excl. fees & taxes)
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New 1 BD Downtown Beach-town Apartment Nov 2023
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Beach Downtown Pet-friendly 1 Bedroom Apartment at 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground, and two dog parks.

1 Bedroom
1 Bathroom
5IconIconIconIconIcon
2 reviews
$95 - $212 / night
(excl. fees & taxes)
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Beach Downtown Pet-friendly @ The Park Home
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Beach Downtown Sarasota Pet-friendly Home @ 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground & two dog parks.

3 Bedrooms
3½ Bathrooms
5IconIconIconIconIcon
22 reviews
$213 - $566 / night
(excl. fees & taxes)
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Beachtown Pet-Friendly Downtown Home @ The Park
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Beach-town Pet-Friendly Downtown Sarasota Home @ 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground & two dog parks.

3 Bedrooms
3½ Bathrooms
5IconIconIconIconIcon
26 reviews
$213 - $566 / night
(excl. fees & taxes)
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Beach Downtown Pet-friendly 1 BD @ The Park
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Beach Downtown Pet-friendly 1 Bedroom Apartment at 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground, and two dog parks.

1 Bedroom
1 Bathroom
4.86IconIconIconIconIcon
14 reviews
$95 - $263 / night
(excl. fees & taxes)
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Tropical Escape Sarasota
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Real Florida Up Close!

3 Bedrooms
2 Bathrooms
$135 - $274 / night
(excl. fees & taxes)
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Condo with a View on Longboat Key
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Kick Back and Relax

0 Bedroom
1 Bathroom
4.98IconIconIconIconIcon
122 reviews
$225 - $275 / night
(excl. fees & taxes)
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Turtle Crawl Inn 63
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Beach Front Condo Paradise. Ground Floor. Studio.

0 Bedroom
1 Bathroom
4.74IconIconIconIconIcon
88 reviews
$198 - $275 / night
(excl. fees & taxes)
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Turtle Crawl Inn 64
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Beach Front One Bedroom Condo Paradise. Fully Remodeled.

1 Bedroom
1 Bathroom
4.88IconIconIconIconIcon
73 reviews
$229 - $389 / night
(excl. fees & taxes)
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Panoramic Gulf View with Amazing Sunset.
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Spacious Condo, 1 huge Bedroom, 2 very comfortable Queen beds. One Sofa sleeper in the living room. What you see is what you get to view every day.

1 Bedroom
1 Bathroom
4.84IconIconIconIconIcon
188 reviews
$229 - $390 / night
(excl. fees & taxes)
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Gulf-to-Bay Living on Longboat Key
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Waterfront condo paradise. Island living. Ground floor. 2 Bd, 2 Ba. Private harbour community, 4 heated pools, Gulf-front pavilion.

2 Bedrooms
2 Bathrooms
$180 / night
(excl. fees & taxes)
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Golf Course Condo
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Breath taking view of the Golf Course and water with nature sounds...

2 Bedrooms
2 Bathrooms
$116 / night
(excl. fees & taxes)
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Tropical Beach Condo!
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Peaceful and Serene

1 Bedroom
1 Bathroom
5IconIconIconIconIcon
11 reviews
$200 - $300 / night
(excl. fees & taxes)
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Craig House with Heated Pool
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Craig House with Heated Pool

2 Bedrooms
2 Bathrooms
4.84IconIconIconIconIcon
83 reviews
$150 - $205 / night
(excl. fees & taxes)
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Golf Course and Private Pool Views
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For the Ultimate Vacation Come Stay at Rosedale Golf & Country Club!!

2 Bedrooms
2 Bathrooms
$225 / night
(excl. fees & taxes)
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Welcome to Paradise
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6 miles from Anna Maria Island Beaches

3 Bedrooms
2 Bathrooms
$170 / night
(excl. fees & taxes)
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Cozy Venice Condo
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Cozy Venice Condo

2 Bedrooms
2 Bathrooms
$170 / night
(excl. fees & taxes)
    1 – 20 Rentals