Beach Access Filters Filters Bedrooms 0 + 1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + Bathrooms 0 + 1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + Clear Filters Amenities Beach Access Beachfront Concierge - Available Laptop Friendly Workspace Pool Tennis Court - Community View - Beach View - Water Washer - Private Wifi Pet Friendly Type Condo House Studio Townhouse Villa Apply Filters Where SkyRun Sarasota Florida Greater Sarasota Area Downtown Sarasota Lido Key Longboat Key Beach Castle Parking Sarasota Metro Area Siesta Key - People 2+ Guests 3+ Guests 4+ Guests 5+ Guests 6+ Guests 7+ Guests 8+ Guests 9+ Guests 10+ Guests 0 Pets 1 Pets 2 Pets 3 Pets Search 1-12 of 31 results Show122436 Sort byBedrooms - Low to HighBedrooms - High to LowName - a to zName - z to aDefault (random) Favorites MAP New PropertyFeatured Property The Beach House Sarasota, Florida 2 Bdrms 2 Baths 6 Guests From $841/night incl. feesnext avail Jan 4 – Mar 5, 2027 · 60-night min View Details Las Hermanas 3 Longboat Key, FL 1 Bdrm 1 Baths 4 Guests From $333/night incl. feesnext avail Sep 12–14 · 2-night min 4.3 View Details Imperial Sunsets on Siesta Siesta Key, FL 2 Bdrms 2 Baths 4 Guests From $311/night incl. feesnext avail Sep 5 – Dec 2 · 88-night min View Details Crystal Sands on Siesta Siesta Key, FL 2 Bdrms 2 Baths 6 Guests From $288/night incl. feesnext avail Sep 5–19 · 14-night min 5.0 View Details Featured Property Crescent Siesta Key Charmer Siesta Key, FL 3 Bdrms 2 Baths 6 Guests From $394/night incl. feesnext avail Sep 5–12 · 7-night min 4.9 View Details Sea La Vie Siesta Key, FL 3 Bdrms 2 Baths 9 Guests 5.0 View Details New Property Sole Retreat Siesta Key, Florida 2 Bdrms 2 Baths 6 Guests From $305/night incl. feesnext avail Sep 5–12 · 7-night min View Details New Property Beach Haven at Beach Castle #21 Longboat Key, Florida 2 Bdrms 2 Baths 8 Guests From $330/night incl. feesnext avail Sep 6–8 · 2-night min View Details New Property Turtle Beach Bliss Siesta Key, Florida 2 Bdrms 2 Baths 4 Guests From $224/night incl. feesnext avail Sep 5–12 · 7-night min 5.0 View Details New Property My Happy Place Siesta Key, Florida 2 Bdrms 2 Baths 4 Guests From $236/night incl. feesnext avail Sep 5–9 · 4-night min 5.0 View Details New Property Siesta Treasure Siesta Key, Florida 4 Bdrms 2 Baths 8 Guests From $535/night incl. feesnext avail Sep 5–8 · 3-night min View Details Featured Property The Windward House Siesta Key, FL 3 Bdrms 2 Baths 6 Guests From $431/night incl. feesnext avail Sep 7–11 · 4-night min 5.0 View Details Search while moving Prev123LastNext
