Search results; Over 1,000 homes in Siesta Key

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Guest favorite
Home in Siesta Key
Designer Home| Sleeps 10| Walk to Beach & Village|
10 guests3 bedrooms4 beds3.5 baths
Aug 16 – 21
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Aug 16 – 21
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R70,713 ZAR for 5 nights

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Top guest favorite
Home in Sarasota
Sarasota Escape | Minutes to Beaches + Downtown
4 beds
Aug 11 – 16
R49,905 ZAR for 5 nights
5.0 out of 5 average rating, 22 reviews
Top guest favorite
Condo in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
1 queen bed
Aug 10 – 15
R22,062 ZAR for 5 nights
4.96 out of 5 average rating, 48 reviews
Guest favorite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
4 beds
Aug 23 – 28
R30,791 ZAR for 5 nights
4.88 out of 5 average rating, 42 reviews
Guest favorite
Home in Sarasota
Tiki Bar Paradise! Heated Pool & Gaming Oasis!
4 beds
Oct 5 – 10
R40,894 ZAR for 5 nights
4.93 out of 5 average rating, 45 reviews
Guest favorite
Condo in Siesta Key
Spacious 2BR 2nd floor Siesta Key condo - GBB 1274
2 beds
Sep 6 – 13
R26,205 ZAR for 7 nights
5.0 out of 5 average rating, 7 reviews
Top guest favorite
Condo in Sarasota
Just renovated 2bed/2bath Siesta Key Beach Condo
4 beds
Sep 2 – 7
R24,474 ZAR for 5 nights
5.0 out of 5 average rating, 13 reviews
Superhost
Bungalow in Siesta Key
Lagoon, pool, the Catamaran at Siesta Key Bungalow
2 beds
Sep 26 – Oct 1
R17,260 ZAR for 5 nights
4.89 out of 5 average rating, 9 reviews
Top guest favorite
Apartment in Sarasota
Modern Luxury Apartment in a House Near Siesta
1 king bed
Aug 20 – 25
R14,259 ZAR for 5 nights
5.0 out of 5 average rating, 200 reviews
Guest favorite
Condo in Siesta Key
Siesta Key Beach - Crescent Royale
2 beds
Sep 16 – 21
R25,325 ZAR for 5 nights
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Vacation home in Siesta Key
The Boat House, Waterfront, Walk to beach!
6 king beds
Aug 14 – 19
R104,811 ZAR for 5 nights
5.0 out of 5 average rating, 34 reviews
Guest favorite
Home in Sarasota
Quiet Oasis | Saltwater Pool + Beaches | 2GB WIFI
5 beds
Aug 22 – 27
R27,164 ZAR for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Condo in Siesta Key
Enchanting Coastal Ambiance & Breathtaking Sunsets
1 bed
Aug 10 – 15
R19,239 ZAR for 5 nights
4.89 out of 5 average rating, 57 reviews
Top guest favorite
Apartment in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
4 beds
Aug 18 – 23
R46,287 ZAR for 5 nights
4.99 out of 5 average rating, 189 reviews
Guest favorite
Condo in Siesta Key
Siesta Key Serenity At The Palm Bay Club
3 beds
Aug 19 – 24
R20,133 ZAR for 5 nights
4.93 out of 5 average rating, 150 reviews
Top guest favorite
Home in Siesta Key
Coastal Elegance Pool Home in Sarasota
4 beds
Aug 12 – 19
R94,613 ZAR for 7 nights
5.0 out of 5 average rating, 10 reviews
Home in Sarasota
Fresh Coastal Comfort | Beaches Close & Bay Views
5 beds
Aug 2 – 7
R22,538 ZAR for 5 nights
New place to stay
Top guest favorite
Home in Sarasota
Your DreamOasisAwaits: SiestaKeyEscape with Pool!
3 beds
Aug 20 – 25
R38,307 ZAR for 5 nights
4.97 out of 5 average rating, 71 reviews
Top guest favorite
Condo in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
1 king bed
Aug 25 – 30
R23,346 ZAR for 5 nights
5.0 out of 5 average rating, 120 reviews