Search results; Over 1,000 homes in Siesta Key

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Guest favorite
Condo in Siesta Key
Perfect Location in Siesta Key
6 guests2 bedrooms5 beds2 baths
Sep 8 – 13
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Sep 8 – 13
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ﺩ.ﺇ8,029 for 5 nights

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Guest favorite
Home in Siesta Key
[lounge like locals]walk to siesta beach +bikes
2 beds
Sep 2 – 7
ﺩ.ﺇ3,171 for 5 nights
4.9 out of 5 average rating, 141 reviews
Guest favorite
Townhouse in Siesta Key
100 Steps to beach access & 5-min Village walk
2 beds
Sep 11 – 16
ﺩ.ﺇ4,371 for 5 nights
4.97 out of 5 average rating, 32 reviews
Top guest favorite
Condo in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
1 king bed
Sep 12 – 17
ﺩ.ﺇ4,921 for 5 nights
5.0 out of 5 average rating, 124 reviews
Superhost
Apartment in Siesta Key
Beach View across street from beach
1 king bed
Sep 8 – 13
ﺩ.ﺇ3,610 for 5 nights
5.0 out of 5 average rating, 4 reviews
Home in Siesta Key
Renovated Villa | Pool & Dock | Easy Walk to Beach
2 queen beds
Sep 9 – 15
ﺩ.ﺇ6,940 for 6 nights
Top guest favorite
Home in Siesta Key
Designer Home| Sleeps 10| Walk to Beach & Village|
4 beds
Sep 1 – 6
ﺩ.ﺇ14,305 for 5 nights
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Home in Sarasota
Your DreamOasisAwaits: SiestaKeyEscape with Pool!
3 beds
Sep 2 – 7
ﺩ.ﺇ6,983 for 5 nights
4.97 out of 5 average rating, 77 reviews
Superhost
Condo in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
3 beds
Sep 7 – 12
ﺩ.ﺇ7,749 for 5 nights
4.9 out of 5 average rating, 99 reviews
Guest favorite
Cottage in Siesta Key
The Marlin: Heated Pool, 4 Houses to Beach
1 king bed
Sep 1 – 6
ﺩ.ﺇ3,845 for 5 nights
4.93 out of 5 average rating, 117 reviews
Superhost
Apartment in Siesta Key
LUXECottage @Crystal Sands -Siesta Key Beachfront!
2 beds
Sep 28 – Oct 3
ﺩ.ﺇ4,837 for 5 nights
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Condo in Siesta Key
On the Beach; Siesta Key SunBum Studio
2 beds
Oct 12 – 17
ﺩ.ﺇ5,248 for 5 nights
4.97 out of 5 average rating, 331 reviews
Superhost
Condo in Siesta Key
A New Listing - Siesta Key Beach Front!
3 beds
Sep 15 – 20
ﺩ.ﺇ8,374 for 5 nights
5.0 out of 5 average rating, 5 reviews
Guest favorite
Condo in Siesta Key
Amazing SK beach views... Newly renovated condo!!!
4 beds
Sep 6 – 12
ﺩ.ﺇ5,802 for 6 nights
4.98 out of 5 average rating, 59 reviews
Guest favorite
Guest suite in Sarasota
Cozy Pied a Terre - walk to beach, shops & dining!
1 queen bed
Sep 19 – 24
ﺩ.ﺇ1,899 for 5 nights
4.78 out of 5 average rating, 145 reviews
Top guest favorite
Condo in Siesta Key
Casa Mar Steps 2 Siesta Key, Pool, Tennis, & More!
2 beds
Sep 6 – 11
ﺩ.ﺇ3,810 for 5 nights
4.95 out of 5 average rating, 82 reviews
Top guest favorite
Home in Sarasota
Palm Tree Haven
2 beds
Sep 8 – 13
ﺩ.ﺇ3,326 for 5 nights
4.98 out of 5 average rating, 59 reviews
Guest favorite
Condo in Siesta Key
Siesta Dunes 1st Floor Beach Front Retreat + Bikes
4 beds
Sep 29 – Oct 6
ﺩ.ﺇ8,244 for 7 nights
4.98 out of 5 average rating, 46 reviews
Guest favorite
Home in Siesta Key
[escape to paradise] siesta key beach getaway
3 beds
Sep 2 – 7
ﺩ.ﺇ3,023 for 5 nights
4.88 out of 5 average rating, 123 reviews