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Siesta Key
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Search results; Over 1,000 places in Siesta Key
Over 1,000 places in Siesta Key
Guest favorite
Guest favorite
Condo in Siesta Key
NO Stairs, beachfront & short walk to the village!
3 beds
3 beds
Apr 27 – May 2
Apr 27 – May 2
$685
night
$685 per night
4.91 out of 5 average rating, 80 reviews
4.91 (80)
Guest favorite
Guest favorite
Home in Sarasota
Bamboo Bungalow - Ideal Location
3 beds
3 beds
Apr 9 – 14
Apr 9 – 14
$179
night
$179 per night
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Home in Siesta Key
One-of-a-kind*Beach, Village, Dock & Private Pool!
4 beds
4 beds
Apr 6 – 11
Apr 6 – 11
$499
night
$499 per night
5.0 out of 5 average rating, 122 reviews
5.0 (122)
Superhost
Superhost
Home in Sarasota
Modern Beach House, Short Drive to Siesta!
3 beds
3 beds
May 16 – 21
May 16 – 21
$116
night
$116 per night
4.78 out of 5 average rating, 74 reviews
4.78 (74)
Guest favorite
Guest favorite
Island in Sarasota
*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
3 beds
3 beds
Apr 27 – May 2
Apr 27 – May 2
$493
night
$493 per night
4.97 out of 5 average rating, 298 reviews
4.97 (298)
Guest favorite
Guest favorite
Vacation home in Siesta Key
Siesta Beach View : Pineapple Bungalow Efficiency
2 beds
2 beds
Apr 11 – 16
Apr 11 – 16
$435
night
$435 per night
5.0 out of 5 average rating, 55 reviews
5.0 (55)
Guest favorite
Guest favorite
Home in Sarasota
Hidden Gem in Sarasota
4 beds
4 beds
Apr 5 – 10
Apr 5 – 10
$283
night
$283 per night
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Home in Sarasota
Urban Oasis, Pool, 6mi>Beach
5 beds
5 beds
Apr 22 – 27
Apr 22 – 27
$365
night
$365 per night
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Guest favorite
Guest favorite
Home in Anna Maria
ami skyview
4 beds
4 beds
Sep 2 – 7
Sep 2 – 7
$850
night
$850 per night
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Guest favorite
Guest favorite
Home in Siesta Key
Beachfront 180-Degree View, Walk to Village!
5 beds
5 beds
Apr 13 – 20
Apr 13 – 20
$625
night
$625 per night
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Home in Longboat Key
Longboat Key Beach Bliss Retreat
Jan 24 – 31
Jan 24 – 31
$235
night
$235 per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favorite
Guest favorite
Home in Bradenton
Pool, Mins to Beaches, Shops, Parks
3 beds
3 beds
May 31 – Jun 5
May 31 – Jun 5
$249
night
$249 per night
4.95 out of 5 average rating, 20 reviews
4.95 (20)
Guest favorite
Guest favorite
Home in Bradenton
Oasis home, 20 min-Anna Maria, Arcade, Bunks
6 beds
6 beds
Apr 7 – 12
Apr 7 – 12
$132
$106
night
$106 per night, originally $132
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favorite
Guest favorite
Home in Bradenton
Coastal Oasis: Cheerful 3Bedroom, Pool, Large Yard
4 beds
4 beds
May 2 – 7
May 2 – 7
$247
night
$247 per night
5.0 out of 5 average rating, 44 reviews
5.0 (44)
Guest favorite
Guest favorite
Home in Sarasota
Sarasota Escape
4 beds
4 beds
May 14 – 19
May 14 – 19
$131
night
$131 per night
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Guest favorite
Guest favorite
Home in Sarasota
Bahia Vista Retreat🌴large home, sleeps 8-9
5 beds
5 beds
Apr 21 – 26
Apr 21 – 26
$175
night
$175 per night
4.96 out of 5 average rating, 70 reviews
4.96 (70)
Guest favorite
Guest favorite
Condo in Bradenton
Bradenton Beach, Anna Maria Island, IMG Academy!
2 king beds
2 king beds
May 22 – 27
May 22 – 27
$125
night
$125 per night
4.93 out of 5 average rating, 54 reviews
4.93 (54)
Guest favorite
Guest favorite
Home in Bradenton
Large 4 BD heat pool near Anna Maria Island + IMG
5 beds
5 beds
Apr 23 – 28
Apr 23 – 28
$239
night
$239 per night
4.96 out of 5 average rating, 28 reviews
4.96 (28)
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